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On the Hydrostannylation of Aryl Propargylic Alcohols and Their Derivatives: Remarkable Differences in Both Regio‐ and Stereoselectivity in Radical‐ and Nonradical‐Mediated Transformations
Author(s) -
Oderinde Martins S.,
Froese Robert D. J.,
Organ Michael G.
Publication year - 2014
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.201403459
Subject(s) - stereoselectivity , chemistry , aryl , regioselectivity , moiety , steric effects , electronic effect , medicinal chemistry , organic chemistry , catalysis , alkyl
Herein, we describe a highly regio‐ and stereoselective radical‐mediated and molecular‐oxygen (O 2 )‐dependent hydrostannylation of phenyl propargylic alcohols and their derivatives. There is a significant steric effect on the stereoselectivity of the tin‐radical addition. Further, the uncatalyzed regio‐ and stereoselective hydrostannylation of aryl propargylic alcohols with n Bu 3 SnH and Ph 3 SnH is also described and occurs with near titration kinetics. Although the uncatalyzed addition with n Bu 3 SnH gave a remarkable γ‐regioselectivity irrespective of the electronic nature of the aryl moiety, addition with Ph 3 SnH appears to be driven by the electronic nature of the aryl alkynes.