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Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands.

ABSTRACT: Cobalt(II) halides in combination with phenoxy-imine (FI) ligands generated efficient precatalysts in situ for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling between alkyl bromides and neopentylglycol (hetero)arylboronic esters. The protocol enabled efficient C-C bond formation with a host of nucleophiles and electrophiles (36 examples, 34-95%) with precatalyst loadings of 5 mol%. Studies with alkyl halide electrophiles that function as radical clocks support the intermediacy of alkyl radicals during the course of the catalytic reaction. The improved performance of the FI-cobalt catalyst was correlated with decreased lifetimes of cage-escaped radicals as compared to diamine-type ligands. Studies of the phenoxy(imine)-cobalt coordination chemistry validate the L,X interaction leading to the discovery of an optimal, well defined, air-stable mono-FI cobalt(II) precatalyst structure.

SUBMITTER: Mills LR 

PROVIDER: S-EPMC9400687 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Cobalt-Catalyzed C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands.

Mills L Reginald LR   Gygi David D   Ludwig Jacob R JR   Simmons Eric M EM   Wisniewski Steven R SR   Kim Junho J   Chirik Paul J PJ  

ACS catalysis 20220120 3

Cobalt(II) halides in combination with phenoxy-imine (FI) ligands generated efficient precatalysts <i>in situ</i> for the C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Suzuki-Miyaura cross coupling between alkyl bromides and neopentylglycol (hetero)arylboronic esters. The protocol enabled efficient C-C bond formation with a host of nucleophiles and electrophiles (36 examples, 34-95%) with precatalyst loadings of 5 mol%. Studies with alkyl halide electrophiles that function as radical clocks support the in  ...[more]

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