Unexpected ortho-Heck Reaction under the Catellani Conditions

被引：10

作者：

Rago, Alexander J. ^{[1
]}

Dong, Guangbin ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 10期

关键词：

C-H FUNCTIONALIZATION; EFFICIENT SYNTHESIS; ARYL IODIDES; PALLADIUM; ALKYLATION; MIGRATION; 1,4-MIGRATION; PD/NORBORNENE;

D O I：

10.1021/acs.orglett.0c00952

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected ortho-Heck reaction has been discovered during the study of palladium/norbornene (Pd/NBE) catalysis. Under the Catellani reaction conditions in the presence of lithium salts and olefins, Heck coupling takes place at the ortho position instead of the commonly observed ipso position; meanwhile, a norbornyl group is introduced at the arene ipso position. Systematic deuterium labeling and crossover experiments suggest an unusual 1,4-palladium migration/intramolecular hydrogen transfer pathway. The knowledge gained in this study could provide insights for the future development of the Pd/NBE catalysis.

引用

页码：3770 / 3774

页数：5

共 39 条

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