Recent Developments in C‐S, C‐Se Bond Formation via Three‐Component Reactions of Alkynes DOI Open Access
Zhan‐Yong Wang, Guipeng Feng, Xiaoying Jiang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract Alkynes are valuable building blocks in organic synthesis. They can undergo three‐component difunctionalization to create sulfur or selenium‐containing compounds. Three‐component reactions of alkynes atom economic, practical and regioselective. This review will disscuss decade developments, including C−S C−Se bond formation via thiolation, sulfonylation selenylation. Recent developments be mainly categorized into three types. (1) Radical C−S/S−Se is a hot topic. Reactions initiated by S/Se radicals other exhibit two types selectivities. Photochemical electrochemical under eco‐friendly conditions have been increasingly reported. (2) Some transformations involve electrophilic three‐membered ring intermediates. Thiiraniums, seleniraniums, iodoniums among the most prevalent species. ring‐opening various nucleophiles participate tandem reactions. (3) Metal‐catalyzed reactions, classic category, also discussed text. In following section, we provide an overview based on mechanisms substrates. The roles added reagents discussed.

Language: Английский

Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover DOI Open Access
Pierre Palamini, Alexandre A. Schoepfer, Jérôme Waser

et al.

Angewandte Chemie International Edition, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2-azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Language: Английский

Citations

0
Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover DOI Open Access
Pierre Palamini, Alexandre A. Schoepfer, Jérôme Waser

et al.

Angewandte Chemie, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Abstract The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical‐polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2‐azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Language: Английский

Citations

0
Recent Developments in C‐S, C‐Se Bond Formation via Three‐Component Reactions of Alkynes DOI Open Access
Zhan‐Yong Wang, Guipeng Feng, Xiaoying Jiang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract Alkynes are valuable building blocks in organic synthesis. They can undergo three‐component difunctionalization to create sulfur or selenium‐containing compounds. Three‐component reactions of alkynes atom economic, practical and regioselective. This review will disscuss decade developments, including C−S C−Se bond formation via thiolation, sulfonylation selenylation. Recent developments be mainly categorized into three types. (1) Radical C−S/S−Se is a hot topic. Reactions initiated by S/Se radicals other exhibit two types selectivities. Photochemical electrochemical under eco‐friendly conditions have been increasingly reported. (2) Some transformations involve electrophilic three‐membered ring intermediates. Thiiraniums, seleniraniums, iodoniums among the most prevalent species. ring‐opening various nucleophiles participate tandem reactions. (3) Metal‐catalyzed reactions, classic category, also discussed text. In following section, we provide an overview based on mechanisms substrates. The roles added reagents discussed.

Language: Английский

Citations

1