Journal
ACS CATALYSIS
Volume 7, Issue 3, Pages 1681-1692Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02988
Keywords
immobilized phosphines; polystyrene; bisphosphine; first-row transition metals; C-N coupling; C-H/C-Ocoupling; hydroboration
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Funding
- JSPS KAKENHI [JP25810056, JP151-105801]
- ACT-C
- CREST from JST
- Tosoh Organic Chemical Co., Ltd.
- Grants-in-Aid for Scientific Research [16K13988] Funding Source: KAKEN
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A polystyrene-cross-linking bisphosphine PSDPPBz was synthesized through radical emulsion copolymer-ization between 4-t-butylstyrene as a monomer and tetraviny-lated 1,2-bis(diphenylphosphino)benzene (DPPBz) as a 4-fold cross-linker. The location of the DPPBz bisphosphine moiety at the branching points of the cross-linked network organic polymer allowed controlled bisphosphine monochelation to transition metals under conditions where homogeneous ligands may form bischelated single metal complexes or multinuclear complexes. PS-DPPBz showed high ligand performance in first-row transition metal catalysis, enabling challenging molecular Alkyl transformations that were not possible through the screening of existing homogeneous ligands. In the Ni-catalyzed amination of aryl chlorides with N-alkyl-substituted primary amines, the substrate scope has been expanded to include 2,6-disubstituted aryl chlorides and N-tertiary-alkyl-substituted primary amines. PS-DPPBz was effective for the Ni-catalyzed C-H/C-O coupling between 1,3-azoles and monocyclic aryl pivalates, which showed poor reactivity in the reported homogeneous catalytic system based on 1,2-bis(dicyclohexylphosphino)ethane (DCYPE). The usefulness of the polymer-cross-linking strategy was also demonstrated in alkene hydroboration reactions catalyzed by Cu or Co.
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