Anti-Markovnikov hydroheteroarylation of unactivated alkenes with indoles, pyrroles, benzofurans, and furans catalyzed by a nickel-N-heterocyclic carbene system

Journal of the American Chemical Society
York SchrammJohn F Hartwig

Abstract

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 α-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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Citations

Feb 9, 2016·Journal of the American Chemical Society·Li-Jun XiaoQi-Lin Zhou
Aug 31, 2016·Topics in Current Chemistry·Junichiro YamaguchiKenichiro Itami
Oct 7, 2016·Journal of the American Chemical Society·Kin S YangKeary M Engle
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong
Jun 15, 2017·Journal of the American Chemical Society·Matthew R Elsby, Samuel A Johnson
Mar 12, 2016·Organic & Biomolecular Chemistry·Sudam Ganpat DawandeSreenivas Katukojvala
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Oct 6, 2020·Angewandte Chemie·Sergio Cuesta-GalisteoCristina Nevado
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