A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin

被引：15

作者：

Cain, David L. ^{[1
]}

McLaughlin, Calum ^{[2
]}

Molloy, John J. ^{[2
]}

Carpenter-Warren, Cameron ^{[1
]}

Anderson, Niall A. ^{[3
]}

Watson, Allan J. B. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

[2] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[3] GlaxoSmithKline, Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

来源：

SYNLETT | 2019年 / 30卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

Bpin; cascade; cross-coupling; Diels-Alder; Suzuki-Miyaura; ALDER/CROSS-COUPLING REACTIONS; DOMINO REACTIONS;

D O I：

10.1055/s-0037-1611228

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross-coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels-Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

引用

页码：787 / 791

页数：5

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