Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 38, Pages 12215-12218Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b08039
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Funding
- Office of Science, of the U.S. Department of Energy [DE-AC02-05CH11231]
- MEXT [15H05799]
- JST
- SNSF
- Grants-in-Aid for Scientific Research [15H05799] Funding Source: KAKEN
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We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)(2) and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to alpha-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.
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