Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes

The use of isocyanides
as acceptor groups in metal–hydride
hydrogen atom transfer (MHAT) coupling reactions with nonactivated
alkenes to form heterocycles is described. Monosubstituted alkenes
couple and cyclize directly, whereas more substituted alkenes proceed
via a two-step, one-pot procedure involving MHAT reductive cyclization
followed by a MHAT Minisci coupling upon the addition of acid. To
highlight the utility of the methodology, a diverse variety of substituted
heterocycles such as phenanthridines, indoles, and isoquinolines were
prepared.