Stereoselective Fluoroalkylacylation of Alkynes via Cooperative N-Heterocyclic Carbene/Palladium Catalysis

被引：6

作者：

Huang, Ying ^{[1
,2
]}

Wang, Xin-Han ^{[1
,2
]}

Zhang, Chun-Lin ^{[1
]}

Ye, Song ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, CAS Res Educ Ctr Excellence Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci ,Inst Chem, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 16期

基金：

中国国家自然科学基金;

关键词：

ALPHA-METHYLENATION; BETA-HYDROXYLATION; HYDROACYLATION; ALDEHYDES; FLUORINE; EFFICIENT; ALKENES; KETONES; ENALS;

D O I：

10.1021/acs.orglett.4c00875

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a cooperative N-heterocyclic carbene- and palladium-catalyzed three-component reaction of alkynes with aldehydes and fluoroalkyl iodides is developed. A series of biologically valuable CF2 R-incorporated alpha-substituted enones was obtained in moderate to good yields. This mild catalytic method exhibits exclusive regio- and stereoselectivity, excellent functional group tolerance, and a broad substrate scope including terminal and internal alkynes. Mechanistic investigations disclose that this alkyne fluoroalkylacylation proceeds via a radical relay process in which vinyl iodides serve as putative reaction intermediates.

引用

页码：3441 / 3446

页数：6

共 56 条

[31] Single-Electron Transfer Reactions Enabled by N-Heterocyclic Carbene Organocatalysis [J].