Manganese-Mediated Homolytic Aromatic Substitution with Phosphinylidenes

Olivier Berger; Jean-Luc Montchamp

doi:10.1002/tcr.201700021

Manganese-Mediated Homolytic Aromatic Substitution with Phosphinylidenes

Chem Rec. 2017 Dec;17(12):1203-1212. doi: 10.1002/tcr.201700021. Epub 2017 Jun 12.

Authors

Olivier Berger¹, Jean-Luc Montchamp¹

Affiliation

¹ Department of Chemistry and Biochemistry, Texas Christian University, TCU Box 298860, Fort Worth, Texas, 76133, USA.

PMID: 28605572
DOI: 10.1002/tcr.201700021

Abstract

Carbon-phosphorus (C-P) bond-forming reactions via homolytic aromatic substitution (HAS) of non-functionalized substrates with phosphinylidene P(O)H compounds is becoming a useful synthetic tool for the preparation of aryl and heteroaryl phosphonates, phosphinates, and phosphine oxides. This review specifically covers recent work using manganese-mediated free radical processes. Several research groups employ expensive Mn(OAc)₃ , whereas our own contributions focus on the novel and inexpensive Mn(OAc)₂ /MnO₂ system.

Keywords: arylation; homolytic aromatic substitution; manganese; phosphinate; phosphonate.

Publication types

Review