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Complex‐Induced Proximity Effect in the Regioselective Lithiation of Pyridine Derivatives
Author(s) -
Dhau Jaspreet S.,
Singh Amritpal,
Kasetti Yoganjaneyulu,
Bharatam P. V.
Publication year - 2012
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.201101592
Subject(s) - chemistry , regioselectivity , pyridine , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The regioselective ring lithiation of BF 3 ‐complexed 3‐picoline ( 1a ), 3,4‐lutidine ( 1b ), and 3,5‐lutidine ( 1c ) was studied. The dilithiation of 1a , 1b , and 1c was also investigated to experimentally explore the relative preference of the sites on the substituted pyridine ring for lithiation. The role of the complex‐induced proximity effect (CIPE) for inducing lithiation in these moieties was investigated using both experimental and computational studies.