Anti-Markovnikov hydroheteroarylation of unactivated alkenes with indoles, pyrroles, benzofurans, and furans catalyzed by a nickel-N-heterocyclic carbene system.
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.
Division of Chemical Sciences, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.|Department of Chemistry, University of California , Berkeley, California 94720, United States.
York
Y
Schramm
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Makoto
M
Takeuchi
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Kazuhiko
K
Semba
Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.|ACT-C, Japan Science and Technology Agency , 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
Yoshiaki
Y
Nakao
Division of Chemical Sciences, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.|Department of Chemistry, University of California , Berkeley, California 94720, United States.
John F
JF
Hartwig
D000475:Alkenes / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
D000475:Alkenes; D001572:Benzofurans; D005663:Furans; D007211:Indoles; D009942:Organometallic Compounds; D011758:Pyrroles; C030011:carbene; D009532:Nickel; D008697:Methane