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Efficient Synthesis of Thioesters and Amides from Aldehydes by Using an Intermolecular Radical Reaction in Water
Author(s) -
Nambu Hisanori,
Hata Kayoko,
Matsugi Masato,
Kita Yasuyuki
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400754
Subject(s) - chemistry , ammonium bromide , bromide , pulmonary surfactant , intermolecular force , radical , propane , organic chemistry , thioester , combinatorial chemistry , molecule , biochemistry , enzyme
The combination of the water‐soluble radical initiator, 2,2′‐azobis[2‐(2‐imidazolin‐2‐yl)propane] dihydrochloride (VA‐044) and the surfactant, cetyltrimethyl‐ammonium bromide (CTAB), was found to be the most suitable condition for the effective and direct synthesis of useful active thioesters (pentafluorophenyl thioesters) in water. In addition, the direct amidation of aldehydes was achieved by the addition of the amines to the thioesterification reaction mixture in water.