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Review article

Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions

Mandy‐Nicole BirkholzUniversity of Amsterdam, Institute of Molecular Chemistry, Nieuwe Achtergracht 166, 1018 WV, Amsterdam, The NetherlandsZoraida FreixaInstitute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, Tarragona, SpainPiet W. N. M. van LeeuwenInstitute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, Tarragona, Spain
2009en
ABI

Abstract

Catalytic reactions of C-C and C-X bond formation are discussed in this critical review with particular emphasis on cross coupling reactions catalyzed by palladium and wide bite angle bidentate diphosphine ligands. Especially those studies have been collected that allow comparison of the ligand bite angles for the selected ligands: dppp, BINAP, dppf, DPEphos and Xantphos. Similarities with hydrocyanation and CO/ethene/MeOH reactions have been highlighted, while rhodium hydroformylation has been mentioned as a contrasting example, in which predictability is high and steric and electronic effects follow smooth trends. In palladium catalysis wide bite angles and bulkiness of the ligands facilitate generally the reductive elimination thus giving more efficient cross coupling catalysis (174 references).

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Cited by 20 references