Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp3)–H Bonds | Zendy

Scott M. Thullen | Zendy; Sean M. Treacy | Zendy; Tomislav Rovis | Zendy

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Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp³)–H Bonds

Author(s) -

Scott M. Thullen,

Sean M. Treacy,

Tomislav Rovis

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.9b07014

Subject(s) - chemistry , regioselectivity , selectivity , alkylation , catalysis , amide , alkyl , hydrogen bond , yield (engineering) , hydrogen atom , surface modification , combinatorial chemistry , nickel , medicinal chemistry , stereochemistry , photochemistry , organic chemistry , molecule , materials science , metallurgy

The functionalization of unactivated C( sp 3 )-H bonds poses a significant challenge due to their ubiquity and relative similarity in most organic frameworks. Herein, we describe the use of a combined photoredox and nickel catalytic system for the regioselective C( sp 3 )-C( sp 3 ) coupling of unactivated C( sp 3 )-H bonds and alkyl bromides. Positional selectivity is dictated by a 1,5-hydrogen atom transfer (HAT) reaction by a pendent amide. Interception of this radical by a Ni catalyst allows distal alkylation to occur in good yield and excellent selectivity.

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