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Issue 4, 2009
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Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions

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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).

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

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Article information


Submitted
23 Jun 2008
First published
10 Feb 2009

Chem. Soc. Rev., 2009,38, 1099-1118
Article type
Critical Review

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

M. Birkholz (née Gensow), Z. Freixa and P. W. N. M. van Leeuwen, Chem. Soc. Rev., 2009, 38, 1099
DOI: 10.1039/B806211K

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