Open AccessRegioselective Radical Amino-Functionalizations of Allyl Alcohols via Dual Catalytic Cross-Coupling
Author(s) -
Zuxiao Zhang,
Duong T. Ngo,
David A. Nagib
Publication year - 2021
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.1c00404
Subject(s) - regioselectivity , chemistry , nucleophile , catalysis , amination , radical , combinatorial chemistry , alkyl , photochemistry , organic chemistry
The regioselective amination and cross-coupling of a range of nucleophiles with allyl alcohols has been enabled by a dual catalytic strategy. This approach entails the combined action of an Ir photocatalyst that enables mild access to N-radicals via an energy transfer mechanism, as well as a Cu complex that intercepts the ensuing alkyl radical upon cyclization. Merger of this Cu-catalyzed cross-coupling enables a broad range of nucleophiles (e.g. CN, SCN, N 3 , vinyl, allyl) to engage in radical amino-functionalizations of olefins. Notably, stereo, regio, and kinetic probes provide insights into the nature of this Cu-based radical interception.