期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 24, 页码 8799-8803出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja503944n
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资金
- University of Washington
- NSF [1254636]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1254636] Funding Source: National Science Foundation
We have developed the first catalytic method for anti-Markovnikov hydrobromination of alkynes. The reaction affords terminal E-alkenyl bromides in high yield and with excellent regio- and diastereoselectivity. Both aryl- and alkyl-substituted terminal alkynes can be used as substrates. Furthermore, the reaction conditions are compatible with a wide range of functional groups, including esters, nitriles, epoxides, aryl boronic esters, terminal alkenes, silyl ethers, aryl halides, and alkyl halides. A preliminary study of the reaction mechanism suggests that the hydrobromination reaction involves hydrocupration of an alkyne, followed by the bromination of the alkenyl copper intermediate. This study also suggests that 2-tert-butyl potassium phenoxide functions as a mild catalyst turnover reagent and provides a better understanding of the unique effectiveness of (BrCl2C)(2) among brominating reagents.
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