期刊
ORGANIC LETTERS
卷 22, 期 13, 页码 5235-5239出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01901
关键词
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资金
- National Institutes of Health [5R35GM125052-03]
- ACS PRF Doctoral New Investigator Grant
- Tsinghua University Department of Chemistry
A copper-catalyzed method for the E-selective 1,1-diboration of terminal alkynes is described. The tandem process involves sequential dehydrogenative borylation of the alkyne substrate with HBdan (1,8-diaminonaphthalatoborane), followed by hydroboration with HBpin (pinacolborane). This method proceeds efficiently under mild conditions, furnishing 1,1-diborylalkenes with excellent stereoselectivity and broad functional group tolerance. Taking advantage of the different reactivities of the two boryl moieties, the products can then be employed in stepwise cross-couplings with aryl halides for the stereocontrolled construction of trisubstituted alkenes.
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