Experimental and Theoretical Study on Palladium-Catalyzed C–P Bond Formation via Direct Coupling of Triarylbismuths with P(O)–H Compounds

A novel and highly efficient Pd-catalyzed cross-coupling of triarylbismuths with a variety of P(O)–H compounds has been developed that proceeds smoothly without exclusion of moisture or air and provides a general and powerful tool for the preparation of various valuable arylphosphonates, arylphosphi...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-01, Vol.79 (2), p.608-617
Main Authors: Wang, Tao, Sang, Shuai, Liu, Liu, Qiao, Hongwei, Gao, Yuxing, Zhao, Yufen
Format: Article
Language:English
Subjects:
Bismuth - chemistry
Catalysis
Molecular Structure
Organometallic Compounds - chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Palladium - chemistry
Quantum Theory
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Summary:A novel and highly efficient Pd-catalyzed cross-coupling of triarylbismuths with a variety of P(O)–H compounds has been developed that proceeds smoothly without exclusion of moisture or air and provides a general and powerful tool for the preparation of various valuable arylphosphonates, arylphosphinates, and arylphosphine oxides, with high atom-economy, operational simplicity of the procedure, and good to high yield. The coupling reaction is the first example of transition-metal-catalyzed C–P bond construction using triarylbismuth compounds as substrates. DFT calculations reveal that C–P bond formation is the rate-determing step.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402392t