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Preparation of New Sulfonated Triarylphosphanes: Control of the Selectivity by Structural Assistance
Author(s) -
Gulyás Henrik,
Szöllősy Áron,
Szabó Pál,
Halmos Pál,
Bakos József
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300168
Subject(s) - chemistry , selectivity , aryl , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , alkyl
A synthetic approach for the selective preparation of tri‐, di‐, and monosulfonated triarylphosphanes is presented. PPh n Ar 3− n parent phosphanes ( 1a − 8a ) having aryl rings (Ar) activated by simple electron donating groups (CH 3 , CH 3 O) were prepared by the standard Grignard method. The activated rings could be sulfonated selectively under mild conditions and with short reaction times (0.8−3 h). Using a very simple workup procedure, the corresponding tri‐, di‐, and monosulfonated phosphanes ( 1b − 8b ) were isolated in outstanding yields (88−99%) and found to contain negligible amount of phosphane oxides (0−4%). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)