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Sulfur(IV)‐Mediated Unsymmetrical Heterocycle Cross‐Couplings
Author(s) -
Zhou Min,
Tsien Jet,
Qin Tian
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915425
Subject(s) - sulfur , nucleophile , chemistry , alkyl , trigonal bipyramidal molecular geometry , lewis acids and bases , catalysis , metal , coupling reaction , combinatorial chemistry , reductive elimination , trigonal crystal system , organic chemistry , molecule , crystal structure
Despite the tremendous utilities of metal‐mediated cross‐couplings in modern organic chemistry, coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking – coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, we report a sulfur (IV) mediated cross‐coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily‐accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis‐heteroaryl products in a practical and efficient fashion.