High-Throughput Experimentation in Catalysis and Materials Science

Synthetic Routes to Crystalline Complex Metal Alkyl Carbonates and Hydroxycarbonates via Sol–Gel Chemistry—Perspectives for Advanced Materials in Catalysis

“…The complexity of the structural parameters that influence the catalytic activity under industrially relevant conditions and the fact that only a small and varying fraction of the metallic Cu surface is catalytically active has already been described by Schlögl and co-workers [52]. These findings demonstrate the need for a very detailed parameter study, which can definitely be supported by high throughput technology, [60][61][62] to find and optimize suitable materials for heterogeneous catalysis.…”

Synthetic Routes to Crystalline Complex Metal Alkyl Carbonates and Hydroxycarbonates via Sol–Gel Chemistry—Perspectives for Advanced Materials in Catalysis

“…The complexity of the structural parameters that influence the catalytic activity under industrially relevant conditions and the fact that only a small and varying fraction of the metallic Cu surface is catalytically active has already been described by Schlögl and co-workers [52]. These findings demonstrate the need for a very detailed parameter study, which can definitely be supported by high throughput technology, [60][61][62] to find and optimize suitable materials for heterogeneous catalysis.…”

Microscale High-Throughput Experimentation as an Enabling Technology in Drug Discovery: Application in the Discovery of (Piperidinyl)pyridinyl-1 H -benzimidazole Diacylglycerol Acyltransferase 1 Inhibitors

“…After 2 h, tert-butyl 4-oxopiperidine-1-carboxylate (488 mg, 2.45 mmol, 1.0 equiv) was added dropwise over 10 min as a solution in THF. The final concentration was 0.15 M. After 2 h, the reaction mixture was warmed to room temperature, acidified to pH ∼0 with 1 M HCl, and stirred vigorously for 16 (16). A solution of 2-fluoropyridine-5-carboxaldehyde (284 mg, 2.27 mmol, 1.0 equiv) in DMF (2 mL plus 2 × 0.5 mL to rinse) was added dropwise to a suspension of 4-(trifluoromethyl)phenylene-1,2-diamine (400 mg, 2.27 mmol, 1.0 equiv) and Oxone (907 mg, 1.48 mmol, 0.65 equiv) in DMF and water.…”

“…In reactions with electrophile 16, diversely functionalized nucleophiles were investigated including two pyrrolidines (20,21), a piperidinium chloride salt (22), a primary amine (23), an azetidinium chloride salt (24), and a spiropiperidine bearing a cyclic carbamate (25). Likewise, in reactions with nucleophile 4, diverse pyridyl fluorides were selected bearing ketone (26), acetamide (27), or iodide (29) functionality as well as different heterocycles (16,28,30). Both free bases and hydrochloride reagent salt forms (22,24) were included to better approximate the salt diversity of our compound collection, and we reasoned that the excess of base used would neutralize any acidic salts.…”

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

“…Obviously, the data sets acquired in this work are much too limited to enable the construction of quantitative, predictive structure–reactivity models. Currently, despite significant advances made in the high-throughput screening of reactions on a small scale30 the number of chemistry informer library compounds that can be evaluated is limited by practical considerations arising from the need to isolate and characterize products in order to quantify reaction yields. However, this limitation may not remain for long 31.…”

Synthetic Routes to Crystalline Complex Metal Alkyl Carbonates and Hydroxycarbonates via Sol–Gel Chemistry—Perspectives for Advanced Materials in Catalysis

“…The complexity of the structural parameters that influence the catalytic activity under industrially relevant conditions and the fact that only a small and varying fraction of the metallic Cu surface is catalytically active has already been described by Schlögl and co-workers [52]. These findings demonstrate the need for a very detailed parameter study, which can definitely be supported by high throughput technology, [60][61][62] to find and optimize suitable materials for heterogeneous catalysis.…”

Microscale High-Throughput Experimentation as an Enabling Technology in Drug Discovery: Application in the Discovery of (Piperidinyl)pyridinyl-1 H -benzimidazole Diacylglycerol Acyltransferase 1 Inhibitors

“…After 2 h, tert-butyl 4-oxopiperidine-1-carboxylate (488 mg, 2.45 mmol, 1.0 equiv) was added dropwise over 10 min as a solution in THF. The final concentration was 0.15 M. After 2 h, the reaction mixture was warmed to room temperature, acidified to pH ∼0 with 1 M HCl, and stirred vigorously for 16 (16). A solution of 2-fluoropyridine-5-carboxaldehyde (284 mg, 2.27 mmol, 1.0 equiv) in DMF (2 mL plus 2 × 0.5 mL to rinse) was added dropwise to a suspension of 4-(trifluoromethyl)phenylene-1,2-diamine (400 mg, 2.27 mmol, 1.0 equiv) and Oxone (907 mg, 1.48 mmol, 0.65 equiv) in DMF and water.…”

“…In reactions with electrophile 16, diversely functionalized nucleophiles were investigated including two pyrrolidines (20,21), a piperidinium chloride salt (22), a primary amine (23), an azetidinium chloride salt (24), and a spiropiperidine bearing a cyclic carbamate (25). Likewise, in reactions with nucleophile 4, diverse pyridyl fluorides were selected bearing ketone (26), acetamide (27), or iodide (29) functionality as well as different heterocycles (16,28,30). Both free bases and hydrochloride reagent salt forms (22,24) were included to better approximate the salt diversity of our compound collection, and we reasoned that the excess of base used would neutralize any acidic salts.…”

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

“…Obviously, the data sets acquired in this work are much too limited to enable the construction of quantitative, predictive structure–reactivity models. Currently, despite significant advances made in the high-throughput screening of reactions on a small scale30 the number of chemistry informer library compounds that can be evaluated is limited by practical considerations arising from the need to isolate and characterize products in order to quantify reaction yields. However, this limitation may not remain for long 31.…”

Synthetic Routes to Crystalline Complex Metal Alkyl Carbonates and Hydroxycarbonates via Sol–Gel Chemistry—Perspectives for Advanced Materials in Catalysis

“…The complexity of the structural parameters that influence the catalytic activity under industrially relevant conditions and the fact that only a small and varying fraction of the metallic Cu surface is catalytically active has already been described by Schlögl and co-workers [52]. These findings demonstrate the need for a very detailed parameter study, which can definitely be supported by high throughput technology, [60][61][62] to find and optimize suitable materials for heterogeneous catalysis.…”

Microscale High-Throughput Experimentation as an Enabling Technology in Drug Discovery: Application in the Discovery of (Piperidinyl)pyridinyl-1 H -benzimidazole Diacylglycerol Acyltransferase 1 Inhibitors

“…After 2 h, tert-butyl 4-oxopiperidine-1-carboxylate (488 mg, 2.45 mmol, 1.0 equiv) was added dropwise over 10 min as a solution in THF. The final concentration was 0.15 M. After 2 h, the reaction mixture was warmed to room temperature, acidified to pH ∼0 with 1 M HCl, and stirred vigorously for 16 (16). A solution of 2-fluoropyridine-5-carboxaldehyde (284 mg, 2.27 mmol, 1.0 equiv) in DMF (2 mL plus 2 × 0.5 mL to rinse) was added dropwise to a suspension of 4-(trifluoromethyl)phenylene-1,2-diamine (400 mg, 2.27 mmol, 1.0 equiv) and Oxone (907 mg, 1.48 mmol, 0.65 equiv) in DMF and water.…”

“…In reactions with electrophile 16, diversely functionalized nucleophiles were investigated including two pyrrolidines (20,21), a piperidinium chloride salt (22), a primary amine (23), an azetidinium chloride salt (24), and a spiropiperidine bearing a cyclic carbamate (25). Likewise, in reactions with nucleophile 4, diverse pyridyl fluorides were selected bearing ketone (26), acetamide (27), or iodide (29) functionality as well as different heterocycles (16,28,30). Both free bases and hydrochloride reagent salt forms (22,24) were included to better approximate the salt diversity of our compound collection, and we reasoned that the excess of base used would neutralize any acidic salts.…”

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

“…Obviously, the data sets acquired in this work are much too limited to enable the construction of quantitative, predictive structure–reactivity models. Currently, despite significant advances made in the high-throughput screening of reactions on a small scale30 the number of chemistry informer library compounds that can be evaluated is limited by practical considerations arising from the need to isolate and characterize products in order to quantify reaction yields. However, this limitation may not remain for long 31.…”