2-iodobenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.

Conditions: temp:60.01; pressure:0.00; stir:

Procedure: Reactions were run in 8 x 30 mm glass vial inserts in 96 well-plate Para-dox Aluminum Reaction Blocks. The reaction components were dosed according to the design shown in Figure S2 and Figure S3. First, the catalysts (2 umol per vial) and solid bases (20 umol per vial) were added by dosing 50 uL each of a stock solution in 1,2-dichloroethane (40 mM for catalysts, 0.4 M for bases) via single-channel pipette. The 1,2-dichloroethane was then removed via centrifugal evaporation using a Genevac EZ-2 evaporator (Scientific Products)(method: low boiling point, maximum temperature of 30 C, 10-30 minutes). Parylene-coated stir bars (1.98 x 4.80 mm) were loaded into each pre-dosed vial using a stir bar dispenser (V&P Scientific, catalog number VP 711A-96-1). Stock solutions of sulfonamide and boronic acid (0.1 M in sulfonamide, 0.15 M in boronic acid) were prepared in the respective reaction solvent (MeCN, MeOH, DCE, or EtOAc) and 100 uL were dosed into the reaction plate according to the design. Lastly, liquid bases were dispensed manually via single-channel pipette. The reaction block was sealed and the contents were tumble-stirred at ~600 rpm (3-Position Magnetic Tumble Stirrer, U.S. Series, V&P Scientific, Inc.) for 18 hours at 60 C. After the reaction time had elapsed, the plate was removed from the heat. Upon cooling, 500 uL of biphenyl stock solution (0.05 M in MeCN, 0.25 equiv) was added to each well as external standard. The plate was sealed, inverted 3x, and centrifuged for 5 minutes to partition all solids to the bottom of the wells. Taking care not to agitate the solution, 25 uL from each well was sampled via multi-channel pipettor and dispensed into a Thermo Scientific(TM) 96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis. Centrifugation for 5 min to partition all solids to the bottom of the wells. 25 uL sampled from each well by multi-channel pipette and dispensed into a Thermo ScientificTM96-well 1 mL polypropylene plate (SKU 278743) for analysis. Each well in the analysis plate was diluted with 750 uL MeCN and sealed using a PlateLoc Thermal Microplate Sealer, then subjected to UPLC-MS analysis.