N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones

被引：21
|
作者：
Rajkiewicz, Adam A. [1 ,2 ]
Kalek, Marcin [1 ]
机构：
[1] Univ Warsaw, Ctr New Technol, Banacha 2C, PL-02097 Warsaw, Poland
[2] Univ Warsaw, Fac Chem, Pasteura 1, PL-02093 Warsaw, Poland
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 07期
关键词：
ALKENYL IODONIUM SALTS; NUCLEOPHILIC-SUBSTITUTION REACTION; DIELS-ALDER REACTION; STEREOSELECTIVE-SYNTHESIS; ELECTROPHILIC CARBOFUNCTIONALIZATION; ARYLATION; FUNCTIONALIZATION; VINYLATION; MECHANISM; POWERFUL;
D O I：
10.1021/acs.orglett.8b00447
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
引用
收藏
页码：1906 / 1909
页数：4
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