Rhodium-Catalyzed (4+1) Cycloaddition between Benzocyclobutenones and Styrene-Type Alkenes

被引：19

作者：

Ochi, Shusuke ^{[1
]}

Zhang, Zining ^{[1
]}

Xia, Ying ^{[1
]}

Dong, Guangbin ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, 5735 S Ellis Ave, Chicago, IL 60637 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 22期

关键词：

Benzocyclobutenone; C-C Activation; Indanone; Rhodium Catalysis; Ring Expansion; C-C BOND; ENANTIOSELECTIVE SYNTHESIS; RING EXPANSION; CARBON; INSERTION; ACTIVATION; 2-INDANONES; KETONES; ETHERS; CYCLOBUTENONES;

D O I：

10.1002/anie.202202703

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we describe a unique one-carbon ring-expansion strategy to access multi-substituted 2-indanones from benzocyclobutenones and styrene-type olefins. The use of a cationic "ligandless" rhodium catalyst was the key for both high reactivity and selectivity towards the (4+1) product. Broad functional group tolerance, a good substrate scope, and scalability have been demonstrated. Computation studies reveal that the origin of the (4+1) selectivity is due to a facile beta-H elimination pathway that reduces the overall barrier of the turnover-limiting C-C reductive elimination step.

引用

页数：6

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