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Ortho Substituents Direct Regioselective Addition of Tributyltin Hydride to Unsymmetrical Diaryl (or Heteroaryl) Alkynes: An Efficient Route to Stannylated Stilbene Derivatives
Author(s) -
Alami Mouâd,
Liron Fréderic,
Gervais Marina,
Peyrat JeanFrançois,
Brion JeanDaniel
Publication year - 2002
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 - 10.1002/1521-3773(20020503)41:9<1578::aid-anie1578>3.0.co;2-c
Subject(s) - regioselectivity , steric effects , chemistry , electronic effect , tributyltin hydride , substituent , alkyne , hydride , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , hydrogen
An unprecedented ortho‐directing effect (ODE) in diaryl alkynes 1 (R=electron‐withdrawing or electron‐donating group) promotes regioselective addition of tributyltin hydride to the triple bond and afforded efficiently stannylated unsymmetrical 1,2‐diaryl olefins 2 . The precise contributions of steric, electronic, and coordinative factors, which control this regioselectivity are highlighted. The results are rationalized in terms of electronic polarization across the alkyne bond, induced by the ortho substituent whatever its electronic nature.