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Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
Author(s) -
GarcíaLópez JoséAntonio,
Çetin Meliha,
Greaney Michael F.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410751
Subject(s) - aryne , heteroatom , electrophile , nucleophile , chemistry , aryl , reagent , yield (engineering) , surface modification , combinatorial chemistry , component (thermodynamics) , medicinal chemistry , organic chemistry , catalysis , ring (chemistry) , materials science , alkyl , physics , metallurgy , thermodynamics
Arynes participate in three‐component coupling reactions with N, S, P, and Se functionalities to yield 1,2‐heteroatom‐difunctionalized arenes. Using 2‐iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S‐, Se‐, and N‐nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2‐difunctionalized arenes.