Regioselective Rhodium(I)-Catalyzed Hydroarylation of Protected Allylic Amines with Arylboronic Acids

Tsui, Gavin Chit; Menard, Frederic; Lautens, Mark

doi:10.1021/ol100974f.s001

ol100974f_si_001.pdf (2.22 MB)

Regioselective Rhodium(I)-Catalyzed Hydroarylation of Protected Allylic Amines with Arylboronic Acids

journal contribution

posted on 2010-06-04, 00:00 authored by Gavin Chit Tsui, Frederic Menard, Mark Lautens

A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH]₂ and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity.