Unexpected ortho-Heck Reaction under the Catellani Conditions.,Organic Letters

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Unexpected ortho-Heck Reaction under the Catellani Conditions.
Organic Letters ( IF 4.9 ) Pub Date : 2020-04-02 , DOI: 10.1021/acs.orglett.0c00952
Alexander J Rago ₁ , Guangbin Dong ₁

Affiliation

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.

中文翻译：

在Catellani条件下发生意外的邻-Heck反应。

在研究钯/降冰片烯（Pd / NBE）催化过程中发现了意外的Ortho-Heck反应。在Catellani反应条件下，在锂盐和烯烃的存在下，Heck偶联发生在邻位而不是通常观察到的ipso位置。同时，在芳烃的ipso位置引入了降冰片基。系统的氘标记和交叉实验表明不寻常的1,4-钯迁移/分子内氢转移途径。在这项研究中获得的知识可以为Pd / NBE催化的未来发展提供见识。

更新日期：2020-04-02

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