Open AccessNew Developments on the Hirao Reactions, Especially from “Green” Point of View
Author(s) -
Réka Henyecz,
György Keglevich
Publication year - 2019
Publication title -
current organic synthesis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.292
H-Index - 46
eISSN - 1875-6271
pISSN - 1570-1794
DOI - 10.2174/1570179416666190415110834
Subject(s) - chemistry , phosphine , catalysis , aryl , halide , denticity , ligand (biochemistry) , combinatorial chemistry , coupling reaction , base (topology) , medicinal chemistry , organic chemistry , metal , mathematics , mathematical analysis , biochemistry , alkyl , receptor
The Hirao reaction discovered ca. 35 years ago is an important P-C coupling protocol between dialkyl phosphites and aryl halides in the presence of Pd(PPh3)4 as the catalyst and a base to provide aryl phosphonates. Then, the reaction was extended to other Preagents, such as secondary phosphine oxides and H-phosphinates and to other aryl and hetaryl derivatives to afford also phosphinic esters and tertiary phosphine oxides. Instead of the Pd(PPh3)4 catalyst, Pd(OAc)2 and Ni-salts were also applied as catalyst precursors together with a number of mono- and bidentate P-ligands.