Photochemical Organocatalytic Aerobic Cleavage of C=C Bonds Enabled by Charge-Transfer Complex Formation

被引：35

作者：

Chen, Yi-Xuan ^{[1
]}

He, Jun-Tao ^{[1
]}

Wu, Mei-Chun ^{[1
,2
]}

Liu, Zhi-Lin ^{[1
]}

Tang, Kai ^{[1
]}

Xia, Peng-Ju ^{[3
]}

Chen, Kai ^{[1
]}

Xiang, Hao-Yue ^{[1
,4
]}

Chen, Xiao-Qing ^{[1
]}

Yang, Hua ^{[1
]}

机构：

[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China

[2] Huaihua Univ, Coll Chem & Chem Engn, Huaihua 418008, Hunan, Peoples R China

[3] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, Guilin 541004, Peoples R China

[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 22期

基金：

中国国家自然科学基金;

关键词：

CATALYZED OXIDATIVE CLEAVAGE; SELECTIVE OXIDATION; METAL-FREE; OLEFINS; LIGHT; ALKYNES; EFFICIENT; OXYGEN; OZONE;

D O I：

10.1021/acs.orglett.2c01192

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel visible-light-driven organocatalytic protocol to access aerobic oxidative cleavage of olefins, promoted by sodium benzene sulfinate, is described herein. An array of alkenes smoothly delivered the corresponding aldehydes and ketones under transition-metal-free conditions. Notably, alpha-halo-substituted styrenes proceeded with photoinduced oxidation to finally afford alpha-halo-acetophenones with halogen migration. Crucial to this oxidation was the formation of charge-transfer complexes between sodium benzene sulfinate with molecular O-2 to ultimately deliver the carbonyl products.

引用

页码：3920 / 3925

页数：6

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