Premium
Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In‐Situ Synthesis of Ph 3 PCl 2
Author(s) -
Carle Myriam S.,
Shimokura Grace K.,
Murphy Graham K.
Publication year - 2016
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.201600714
Subject(s) - chemistry , iodobenzene , phosphorane , hypervalent molecule , carboxylic acid , reagent , alcohol , organic chemistry , alkyl , diazo , in situ , catalysis
A novel, in‐situ synthesis of dichlorotriphenylphosphorane (Ph 3 PCl 2 ) is accomplished upon combining PPh 3 and the easily prepared hypervalent iodine reagent iodobenzene dichloride (PhICl 2 ). The phosphorane is selectively generated in the presence of carboxylic acid or alcohol residues to rapidly produce acyl chlorides and alkyl chlorides in high yields. Addition of EtOH, PhOH, BnOH, Et 2 NH or CH 2 N 2 results in the direct synthesis of esters, amides and diazo ketones from carboxylic acids.