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Sulfonated Diphenylphosphanes for Homogeneous Biphasic Catalysis via a Combined Protection/Deprotection Protocol
Author(s) -
Jänsch Helge,
Kannenberg Sven,
Boche Gernot
Publication year - 2001
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 - 10.1002/1099-0690(200108)2001:15<2923::aid-ejoc2923>3.0.co;2-i
Subject(s) - chemistry , hydrolysis , alkyl , oleum , catalysis , oxalate , homogeneous , adduct , oxide , organic chemistry , combinatorial chemistry , thermodynamics , physics
Oxidation of the sulfonated oxygen‐labile alkyl‐ and benzyldiphenylphosphanes 3a − f during hydrolytic workup of the oleum‐containing sulfonation mixture is prevented by “soft” hydrolysis with disodium oxalate or basic aluminum oxide. Furthermore, the use of a protection protocol allows for the synthesis of the air‐stable sulfonated phosphanylborane adducts 6a − f for storage and purification purposes. Deprotection yields the corresponding sulfonated alkyl‐ and benzyldiphenylphosphanes 7a − f .