Open AccessHydroalkylation of Olefins To Form Quaternary Carbons
Author(s) -
Samantha A. Green,
Tucker R. Huffman,
Ruairí O. McCourt,
Vincent van der Puyl,
Ryan A. Shenvi
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b02844
Subject(s) - chemistry , markovnikov's rule , electrophile , alkyl , hydride , catalysis , halide , selectivity , quaternary carbon , organic chemistry , alkylation , hydrogen atom , combinatorial chemistry , metal , medicinal chemistry , enantioselective synthesis , regioselectivity
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp 3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.