DDQ-Mediated Oxidative Radical Cycloisomerization of 1,5-Diynols: Regioselective Synthesis of Benzo[b]fluorenones under Metal-Free Conditions

被引：48
|
作者：
Zhu, Hui
Chen, Zhiyuan [1 ]
机构：
[1] Jiangxi Normal Univ, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Jiangxi, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 03期
基金：
中国国家自然科学基金;
关键词：
4+2 CYCLOADDITION REACTIONS; ELECTROPHILIC CYCLIZATION; KINAMYCIN BIOSYNTHESIS; REARRANGEMENT; DERIVATIVES; DIARYLACETYLENES; ARYL;
D O I：
10.1021/acs.orglett.5b03533
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regio- and chemoselective oxidative cycloisomerization reaction of acyclic 1,5-diynols has been developed. The reaction proceeds under metal-free reaction conditions with high efficiency and broad functional group tolerance, which offers a general and straightforward access to benzo[b]fluorenones under metal-free conditions. The preliminary mechanistic studies revealed the possible involvement of a Meyer-Schuster rearrangement combined with an oxidative radical cyclization.
引用
收藏
页码：488 / 491
页数：4
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