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Haloselective Cross-Coupling via Ni/Photoredox Dual Catalysis.

ABSTRACT: The chemoselective functionalization of polyfunctional aryl linchpins is crucial for rapid diversification. Although well-explored for C_sp² and C_sp nucleophiles, the chemoselective introduction of C_sp³ groups remains notoriously difficult and is virtually undocumented using Ni catalysts. To fill this methodological gap, a "haloselective" cross-coupling process of arenes bearing two halogens, I and Br, using ammonium alkylbis(catecholato)silicates, has been developed. Utilizing Ni/photoredox dual catalysis, C_sp³ -C_sp² bonds can be forged selectively at the iodine-bearing carbon of bromo(iodo)arenes. The described high-yielding, base-free strategy accommodates various protic functional groups. Selective electrophile activation enables installation of a second C_sp³ center and can be done without the need for purification of the intermediate monoalkylated product.

SUBMITTER: Lin K

PROVIDER: S-EPMC5548095 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Haloselective Cross-Coupling via Ni/Photoredox Dual Catalysis.

Lin Kingson K Wiles Rebecca J RJ Kelly Christopher B CB Davies Geraint H M GHM Molander Gary A GA

ACS catalysis 20170707 8

The chemoselective functionalization of polyfunctional aryl linchpins is crucial for rapid diversification. Although well-explored for Csp2 and Csp nucleophiles, the chemoselective introduction of Csp3 groups remains notoriously difficult and is virtually undocumented using Ni catalysts. To fill this methodological gap, a "haloselective" cross-coupling process of arenes bearing two halogens, I and Br, using ammonium alkylbis(catecholato)sili ...[more]

PMID: 28804677

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