期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 36, 页码 19871-19878出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202106107
关键词
alkyne functionalization; copper catalysis; cyclic (alkyl)(amino)carbene; protoboration; protosilylation
资金
- National Institutes of Health [5R35GM125052-04, 5R35GM125052-04S1]
- ACS PRF Doctoral New Investigator Grant
- Kwanjeong Educational Foundation (Graduate Fellowship)
- U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program [DE-SC0009376]
- National Science Foundation [CHE-1800598]
- Agence Nationale de la Recherche [ANR-19-276 CE07-0017]
- SDSU University Graduate Fellowship
- Alfred P. Sloan Foundations University Centre for Exemplary Mentoring
- National Science Foundation Graduate Research Fellowship Program [DGE-1650112]
In this study, a selective copper-catalyzed Markovnikov hydrofunctionalization of terminal alkynes is described, facilitated by strongly donating cyclic (alkyl)(amino)carbene (CAAC) ligands. The reaction allows coupling of both alkyl- and aryl-substituted alkynes with a variety of boryl and silyl reagents with high alpha-selectivity. The versatile intermediates produced are scalable and can participate in various downstream transformations.
Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or reagents, with general solutions lacking. Herein, we describe a selective copper-catalyzed Markovnikov hydrofunctionalization of terminal alkynes that is facilitated by strongly donating cyclic (alkyl)(amino)carbene (CAAC) ligands. Using this method, both alkyl- and aryl-substituted alkynes are coupled with a variety of boryl and silyl reagents with high alpha-selectivity. The reaction is scalable, and the products are versatile intermediates that can participate in various downstream transformations. Preliminary mechanistic experiments shed light on the role of CAAC ligands in this process.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据