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Steric Promotion of Aromatic C–H Bond Activation in Primary Benzylamines
Author(s) -
Dunina Valery V.,
Kuz'mina Lyudmila G.,
Kazakova Marina Yu.,
Gorunova Ol'ga N.,
Grishin Yury K.,
Kazakova Elena I.
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199906)1999:6<1029::aid-ejic1029>3.0.co;2-7
Subject(s) - chemistry , steric effects , benzylamine , yield (engineering) , pyridine , dimer , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
ortho ‐Palladation of a sterically crowded primary benzylamine, α‐phenylneopentylamine, was accomplished in a moderate yield of 50% in the reaction with the weakest of palladation agents (Li 2 PdCl 4 ) under very mild conditions, due to a steric promotion of an aromatic C–H bond activation. The structure of dimer 1a thus formed and the palladacycle conformation were established on the basis of 1 H‐NMR spectroscopy of its mononuclear derivatives with [D 5 ]pyridine ( 3a ) and triphenylphosphane ( 4a ), and an X‐ray investi‐gation of the latter.