Directed ortho Metalation Strategies. Effective Regioselective Routes to 1,2-, 2,3-, and 1,2,3-Substituted Naphthalenes

被引：32

作者：

Groom, Katherine ^{[2
]}

Hussain, S. M. Shakil ^{[2
]}

Morin, Justin ^{[2
]}

Nilewski, Christian ^{[2
]}

Rantanen, Toni ^{[1
]}

Snieckus, Victor ^{[2
]}

机构：

[1] Snieckus Innovat, Kingston, ON K7L 3N6, Canada

[2] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

SUBSTITUTED NAPHTHALENES; LITHIATION; ALKALOIDS; BIARYLS; ALKYNES; BINOL; LINK;

D O I：

10.1021/ol500707w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective synthesis of 2,3-di- and 1,2,3-trisubstituted naphthalenes via Directed ortho Metalation (DoM) strategies of N,N-diethyl-O-naphthy1-2-carbamate (1) is presented. Sequential LiTMP metalation-electrophile quench and s-BuLi/TMEDA (or t-BuLi)-electrophile quench of naphthy1-2-carbamate 1 provides a general route to contiguously substituted naphthalenes (6) with full regioselectivity. Further derivatization via ipso-halodesilylation and Suzuki-Miyaura cross-coupling leads ultimately to substituted halonaphthalenes and benzonaphthopyranones (9).

引用

页码：2378 / 2381

页数：4

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