Direct C(sp(2))-H alkylation of unactivated arenes enabled by photoinduced Pd catalysis

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Despite the fundamental importance of efficient and selective synthesis of widely useful alkylarenes, the direct catalytic C(sp(2))-H alkylation of unactivated arenes with a readily available alkyl halide remains elusive. Here, we report the catalytic C(sp(2))-H alkylation reactions of unactivated arenes with alkyl bromides via visible-light induced Pd catalysis. The reaction proceeds smoothly under mild conditions without any skeletal rearrangement of the alkyl groups. The direct syntheses of structurally diverse linear and branched alkylarenes, including the late-stage phenylation of biologically active molecules and an orthogonal one-pot sequential Pd-catalyzed C-C bond-forming reaction, are achieved with exclusive chemoselectivity and exceptional functional group tolerance. Comprehensive mechanistic investigations through a combination of experimental and computational methods reveal a distinguishable Pd(0)/Pd(I) redox catalytic cycle and the origin of the counter-intuitive reactivity differences among alkyl halides. Direct catalytic C(sp(2))-H alkylation of unactivated arenes with alkyl halides remains elusive despite the progress in C-H functionalization. Here, the authors report the catalytic C(sp(2))-H alkylation of unactivated arenes with alkyl bromides via visible-light induced Pd catalysis.
Publisher
NATURE RESEARCH
Issue Date
2020-10
Language
English
Article Type
Article
Citation

NATURE COMMUNICATIONS, v.11, no.1

ISSN
2041-1723
DOI
10.1038/s41467-020-19038-8
URI
http://hdl.handle.net/10203/278827
Appears in Collection
CH-Journal Papers(저널논문)
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