Synthesis of annelated phospholes through intramolecular C-H activation by monovalent phosphorus

Xinda Wei; Zongming Lu; Xu Zhao; Zheng Duan; Francois Mathey

doi:10.1002/anie.201410603

Synthesis of annelated phospholes through intramolecular C-H activation by monovalent phosphorus

Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1583-6. doi: 10.1002/anie.201410603. Epub 2014 Dec 9.

Authors

Xinda Wei¹, Zongming Lu, Xu Zhao, Zheng Duan, Francois Mathey

Affiliation

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

PMID: 25491758
DOI: 10.1002/anie.201410603

Abstract

Electrophilic terminal phosphinidene complexes [Ar-Ar-P-W(CO)5 ] (Ar-Ar: biaryl or an analogue thereof) undergo a spontaneous insertion of the phosphorus atom into the vicinal CH bonds to give annelated phospholes. Twelve examples are described, including biphenyl, thienyl, pyrrolyl, and benzofuryl groups as biaryl moieties. The activation energy of the insertion reaction is quite low (about 2 kcal mol(-1) ).

Keywords: CH activation; biaryls; insertion; phosphinidenes; phospholes.