期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 14, 期 -, 页码 2259-2265出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.201
关键词
HAT; hydrogen atom transfer; hydrofunctionalization
资金
- National Science Foundation [CHE-1151563]
We show that cobalt bis(acetylacetonate) [Co(acac)(2)], tert-butyl hydroperoxide (TBHP), and triethylsilane (Et3SiH) constitute an inexpensive, general, and practical reagent combination to initiate a broad range of Markovnikov-selective alkene hydrofunctionalization reactions. These transformations are believed to proceed by cobalt-mediated hydrogen atom transfer (HAT) to the alkene substrate, followed by interception of the resulting alkyl radical intermediate with a SOMOphile. In addition, we report the first reductive couplings of unactivated alkenes and aryldiazonium salts by an HAT pathway. The simplicity and generality of the Co(acac)(2)-TBHP-Et3SiH reagent combination suggests it as a useful starting point to develop HAT reactions in complex settings.
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