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Iron‐Catalyzed Reaction of Urea with Alcohols and Amines: A Safe Alternative for the Synthesis of Primary Carbamates
Author(s) -
PeñaLópez Miguel,
Neumann Helfried,
Beller Matthias
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600587
Subject(s) - chemistry , nucleophile , catalysis , phosgene , urea , primary (astronomy) , organic chemistry , combinatorial chemistry , lewis acids and bases , physics , astronomy
A general study of the iron‐catalyzed reaction of urea with nucleophiles is here presented. The carbamoylation of alcohols allows for the synthesis of N ‐unsubstituted (primary) carbamates, including present drugs (Felbamate and Meprobamate), without the necessity to apply phosgene and related derivatives. Using amines as nucleophiles gave rise to the respective mono‐ and disubstituted ureas via selective transamidation reaction. These atom‐economical transformations provide a direct and selective access to valuable compounds from cheap and readily available urea using a simple Lewis‐acidic iron(II) catalyst.