Silver/NBS-Catalyzed Synthesis of α-Alkylated Aryl Ketones from Internal Alkynes and Benzyl Alcohols via Ether Intermediates

被引：9

作者：

Chun, Supill ^{[1
]}

Chung, Young Keun ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Nat Sci, Dept Chem, Seoul 08826, South Korea

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

基金：

新加坡国家研究基金会;

关键词：

BORROWING HYDROGEN; ALPHA; BETA-UNSATURATED KETONES; C-H; HYDRATION; FUNCTIONALIZATION; DEHYDROGENATION; ALDEHYDES; CHLORIDES; REAGENTS; STRATEGY;

D O I：

10.1021/acs.orglett.8b02252

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The silver hexafluoroantimonate/N-bromosuccinimide (NBS)-catalyzed synthesis of alpha-alkylated aryl ketones with a tertiary carbon center from internal alkynes and benzyl alcohols is reported. This reaction proceeds via the etherification of benzyl alcohols with an in situ generated benzyl bromide, formed by the reaction of benzyl alcohol with a catalytic amount of NBS and AgSbF6. Ag-catalyzed C-O cleavage of the ether leads to a tolyl radical, which undergoes addition to the alkyne, ultimately leading to the alpha-alkylated aryl ketone products.

引用

页码：5583 / 5586

页数：4

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