Direct Synthesis of Dialkyl Ketones from Aliphatic Aldehydes through Radical N-Heterocyclic Carbene Catalysis

被引：104

作者：

Kakeno, Yuki ^{[1
]}

Kusakabe, Mayu ^{[1
]}

Nagao, Kazunori ^{[1
]}

Ohmiya, Hirohisa ^{[1
,2
]}

机构：

[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

[2] PRESTO, JST, Saitama 3320012, Japan

来源：

ACS CATALYSIS | 2020年 / 10卷 / 15期

关键词：

N-heterocyclic carbene; organocatalysis; radical; aldehydes; dialkyl ketones; ORGANOCATALYSIS; ACYLATION; MECHANISM;

D O I：

10.1021/acscatal.0c02849

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A designed thiazolium-type N-heterocyclic carbene (NHC) catalyst having an N-neopentyl group and seven-membered backbone structure was achieved through the use of aliphatic aldehydes as acyl donors in the decarboxylative radical coupling with aliphatic carboxylic acid derived-redox active esters. The NHC catalyst also enabled the vicinal alkylacylation of vinyl arenes using aliphatic aldehydes and redox-active esters through a radical relay mechanism. These reactions provided the synthetic route to sterically hindered dialkyl ketones.

引用

页码：8524 / 8529

页数：6

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