Olefination of Alkyl Halides with Aldehydes by Merging Visible-Light Photoredox Catalysis and Organophosphorus Chemistry

被引：13

作者：

Jiang, Min ^{[1
]}

Yang, Haijun ^{[1
]}

Lefebvre, Quentin ^{[2
]}

Su, Jihu ^{[3
]}

Fu, Hua ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

[2] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[3] Univ Sci & Technol China, Dept Modern Phys, CAS Key Lab Microscale Magnet Resonance, Hefei 230026, Anhui, Peoples R China

来源：

ISCIENCE | 2018年 / 6卷

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATIVE COUPLINGS; STEREOSELECTIVE-SYNTHESIS; METATHESIS CATALYSTS; RADICAL-ADDITION; INTERNAL ALKYNES; TERMINAL ALKYNES; SINGLE-LAYER; EFFICIENT; ARYL; FLUORINE;

D O I：

10.1016/j.isci.2018.07.011

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Carbon-carbon double bond (C=C) formation is a crucial transformation in organic chemistry. Visiblelight photoredox catalysis provides economical and sustainable opportunities for the development of novel and peculiar organic reactions. Here we report a method for the olefination of alkyl halides with aldehydes by visible-light photoredox catalysis using triphenylphosphine as a reductive quencher (103 examples). This transformation accommodates a variety of aldehydes including paraformaldehyde; aqueous formaldehyde; 2,2,2-trifluoroacetaldehyde monohydrate; 2,2,2-trifluoro-1-methoxyethanol; and other common aldehydes. The present method exhibits several advantages, including operational simplicity, mild reaction conditions, wide functional group tolerance, and amenability to gram-scale synthesis. We anticipate that it will be widely used in the synthesis of organic molecules, natural products, biological molecules, and polymers.

引用

页码：102 / +

页数：190

共 106 条

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