General principles of ortho-lithiation in arylphosphinamides

0Citations
Citations of this article
5Readers
Mendeley users who have this article in their library.

Abstract

The development of alternatives to render the ortho-lithiation reaction of arylphosphinamides a diastereoselective and enantioselective process turned this class well explored among the organophosphorus compounds. The use of organolithium bases is the most suitable method for ortho functionalization in aromatic systems. In general, the reaction proceeds in two stages. Firstly, the removal of the ortho hydrogen promoted by the organolithium base takes place, followed by electrophilic neutralization leading to the formation of 1,2-disubstituted product. The improvement of the potential of the organolithium bases is often achieved by using chelating agents, such as N,N,N',N'- tetramethylethylenediamine (TMEDA) and (-)sparteine. Despite being subject of many theoretical and experimental studies, the mechanism of ortho-metallation remains controversial. Therefore, this paper will discuss the main mechanisms involved in the ortho-metallation of arylphosphinamides as well as the processes of synthesis of this class of organophosphorus compounds.

Cite

CITATION STYLE

APA

Bastos, N. M. S., Popovici, C. A., De Souza, M. C., & Romeiro, G. A. (2014). General principles of ortho-lithiation in arylphosphinamides. Revista Virtual de Quimica, 6(4), 1086–1104. https://doi.org/10.5935/1984-6835.20140069

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free