Nickel-Catalyzed Csp2Csp3 Bond Formation by CarbonFluorine Activation

We report herein a general catalytic method for Csp2Csp3 bond formation through CF activation. The process uses an inexpensive nickel complex with either diorganozinc or alkylzinc halide reagents, including those with β‐hydrogen atoms. A variety of fluorine substitution patterns and functional gro...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-03, Vol.20 (11), p.3162-3168
Main Authors: Sun, Alex D., Leung, Kaylyn, Restivo, Anita D., LaBerge, Nicole A., Takasaki, Harumi, Love, Jennifer A.
Format: Article
Language:English
Subjects:
Catalysis
Coordination Complexes - chemistry
cross-coupling
fluorine
Fluorine - chemistry
Halogens - chemistry
Molecular Structure
nickel
Nickel - chemistry
synthetic methods
zinc
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Summary:We report herein a general catalytic method for Csp2Csp3 bond formation through CF activation. The process uses an inexpensive nickel complex with either diorganozinc or alkylzinc halide reagents, including those with β‐hydrogen atoms. A variety of fluorine substitution patterns and functional groups can be readily incorporated. Sequential reactions involving different precatalysts and coupling partners permit the synthesis of densely functionalized fluorinated building blocks. Gently does it! A general catalytic method for Csp2Csp3 bond formation through CF activation with an inexpensive nickel complex with either diorganozinc or alkylzinc halide reagents, including those with β‐hydrogen atoms, is described (see scheme; DG = directing group). A variety of fluorine substitution patterns and functional groups (FGs) are readily tolerated. Sequential reactions involving different precatalysts and coupling partners permit the synthesis of densely functionalized fluorinated building blocks.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201303809