Transformations of diphenylphosphinothioic acid tertiary amides mediated by directed ortho metallation

ortho-Lithiation of N,N-diisopropyl-P,P-diphenylphosphinothioic amide using n-BuLi in the presence of TMEDA in diethyl ether followed by electrophilic trapping is described as an efficient method for the synthesis of ortho-functionalised derivatives in high yields. The structural modification of the...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-08, Vol.10 (29), p.5647-5658
Main Authors: el Hajjouji, Hajar, Belmonte, Eva, García-López, Jesús, Fernández, Ignacio, Iglesias, María José, Roces, Laura, García-Granda, Santiago, El Laghdach, Anas, López Ortiz, Fernando
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:ortho-Lithiation of N,N-diisopropyl-P,P-diphenylphosphinothioic amide using n-BuLi in the presence of TMEDA in diethyl ether followed by electrophilic trapping is described as an efficient method for the synthesis of ortho-functionalised derivatives in high yields. The structural modification of the phosphinothioic amide includes C-X (X = P, S, Si, Sn, I) and C-C bond forming reactions with a large variety of electrophiles. Additional applications based on functional group transformations are also reported. They include imine formation, desulfurization and Suzuki cross-coupling reactions on selected compounds.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25395j