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Nucleophile‐Selective Cross‐Coupling Reactions with Vinyl and Alkynyl Bromides on a Dinucleophilic Aromatic Substrate
Author(s) -
He LuYing,
SchulzSenft Mathias,
Thiedemann Birk,
Linshoeft Julian,
Gates Paul J.,
Staubitz Anne
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500138
Subject(s) - chemistry , nucleophile , electrophile , sonogashira coupling , aryl , coupling reaction , nucleophilic aromatic substitution , medicinal chemistry , combinatorial chemistry , organic chemistry , palladium , nucleophilic substitution , catalysis , alkyl
A nucleophile‐selective cross‐coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe 3 , has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki–Miyaura cross‐coupling reaction can take place on the same molecule.