Intramolecular, Pd/Cu-Co-catalyzed P-C Bond Cleavage and Addition onto an Alkyne: A Route to Benzophospholes

Yang Zhou; Zhenjie Gan; Bo Su; Jun Li; Zheng Duan; François Mathey

doi:10.1021/acs.orglett.5b02926

Intramolecular, Pd/Cu-Co-catalyzed P-C Bond Cleavage and Addition onto an Alkyne: A Route to Benzophospholes

Org Lett. 2015 Nov 20;17(22):5722-4. doi: 10.1021/acs.orglett.5b02926. Epub 2015 Nov 11.

Authors

Yang Zhou¹, Zhenjie Gan¹, Bo Su¹, Jun Li¹, Zheng Duan¹, François Mathey^{1

2}

Affiliations

¹ College of Chemistry and Molecular Engineering, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Zhengzhou University , Zhengzhou 450001, P.R. China.
² Nanyang Technological University , Division of Chemistry & Biological Chemistry, 21 Nanyang Link, Singapore 637371.

PMID: 26561234
DOI: 10.1021/acs.orglett.5b02926

Abstract

Under Pd(II)/CuI cocatalysis, o-diarylphosphinophenylalkynes cyclize in boiling toluene via C-P bond cleavage and arylphosphination of the C≡C bond. This protocol provides an unprecedented atom- and step-efficient access to optoelectronically and biologically interesting benzophospholes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry
Catalysis
Combinatorial Chemistry Techniques
Copper / chemistry
Cyclization
Iodides / chemistry
Molecular Structure
Organophosphorus Compounds / chemical synthesis*
Organophosphorus Compounds / chemistry
Palladium / chemistry*

Substances

Alkynes
Benzene Derivatives
Iodides
Organophosphorus Compounds
Palladium
Copper
cuprous iodide