Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.
Direct C(6) alkylation of pyridyl alcohols can be achieved following an initial deprotonation of the hydroxy group. This transformation, which is believed to occur by a Chichibabin-type alkylation, avoids lateral deprotonation prior to pyridine ring alkylation and gives increased regioselectivity for C(6) over C(4) alkylation.
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Jenna L
JL
Jeffrey
Richmond
R
Sarpong
D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D011725:Pyridines; D008094:Lithium