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Pd‐NHC‐Catalyzed Alkynylation of General Aryl Sulfides with Alkynyl Grignard Reagents
Author(s) -
Baralle Alexandre,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2016
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.201602315
Subject(s) - aryl , electrophile , chemistry , alkynylation , organosulfur compounds , reagent , benzofuran , catalysis , combinatorial chemistry , palladium , organic chemistry , carbene , sulfur , alkyl
Cross‐coupling reactions of unactivated aryl sulfides with alkynylmagnesium chloride have been invented to afford 1‐aryl‐1‐alkynes with the aid of a palladium/N‐heterocyclic carbene complex. This reaction has by far the widest scope of all transformations utilizing aryl sulfides and alkynes, while known cross‐coupling alkynylations of aryl‐sulfur electrophiles require activated azaaryl sulfides, thiolactams, or arenesulfonyl chlorides. The alkynylation of aryl sulfides is compatible with typical protecting functional groups. The alkynylation is applied to the synthesis of benzofuran‐based fluorescent molecules by taking advantage of characteristic organosulfur chemistry.