Alpha-heteroarylation of esters, lactones, amides, and lactams by nucleophilic aromatic substitution.
[reaction: see text] A mild and efficient alpha-heteroarylation of simple esters and amides was developed via nucleophilic aromatic substitution. The choice of NaHMDS in toluene gave the best results. A tandem alpha-heteroarylation and hydroxylation protocol using air as the oxidant afforded tertiary alcohols in good yields.
Department of Medicinal Chemistry, Merck Research Laboratories, Merck & Company, Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. hong_shen@merck.com
Hong C
HC
Shen
Fa-Xiang
FX
Ding
Steven L
SL
Colletti
D000388:Air; D000438:Alcohols / Q000138:chemical synthesis*; D000577:Amides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007769:Lactams / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000577:Amides; D004952:Esters; D007769:Lactams; D007783:Lactones; D016877:Oxidants