Zinc catalyzed and mediated propargylations with propargyl boronates.
The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.
Fandrick
Daniel R
DR
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. daniel.fandrick@boehringer-ingelheim.com
Fandrick
Keith R
KR
Reeves
Jonathan T
JT
Tan
Zhulin
Z
Johnson
Courtney S
CS
Lee
Heewon
H
Song
Jinhua J
JJ
Yee
Nathan K
NK
Senanayake
Chris H
CH
D000447:Aldehydes / Q000737:chemistry*; D001889:Borinic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D000447:Aldehydes; D001889:Borinic Acids; D007659:Ketones; D010293:Pargyline; D015032:Zinc