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Cover Feature: A General Catalytic Method for Highly Cost‐ and Atom‐Efficient Nucleophilic Substitutions (Chem. Eur. J. 29/2018)
Author(s) -
Huy Peter H.,
Filbrich Isabel
Publication year - 2018
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.201801931
Subject(s) - reagent , nucleophilic substitution , chemistry , formamide , catalysis , cyanuric chloride , combinatorial chemistry , molecule , alcohol , nucleophilic aromatic substitution , substitution (logic) , alkyl , nucleophile , organic chemistry , chloride , computer science , programming language
Substitution reactions belong to the most fundamental transformations in chemistry. However, they are commonly restricted by a poor sustainability, as at least one waste byproduct is formed. Herein, a general and highly efficient formamide‐catalyzed method for nucleophilic substitution of alcohols furnishing alkyl chlorides is presented, in which the mass of the inevitable byproduct could be reduced to a minimum, through the application of inexpensive cyanuric chloride as reagent in substoichiometric amounts down to 34 mol % with respect to the starting material. Therefore, only one molecule of the reagent is required to convert three molecules of the starting alcohol. Application towards the synthesis of a bioactive compound is also demonstrated. (© Background graphic MrGarry/Shutterstock.com.) More information can be found in the Full Paper by P. H. Huy and I. Fillbrich on page 7410.