A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters.
We have identified a catalyst capable of effecting the rapid, room-temperature cross-coupling between acid fluorides and diorganozinc reagents. The use of acid fluorides as electrophilic partners allows this reaction to tolerate epimerizable functionality as well as beta leaving groups. The same catalyst is also capable of cross-coupling acid chlorides, acyl cyanides, anhydrides, thioesters, and pyridyl esters. Noteworthy is the ability of the reaction to successfully transfer both groups from the organometalic fragment.
Zhang
Yongda
Y
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80526, USA.
Rovis
Tomislav
T
D000812:Anhydrides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013696:Temperature; D015032:Zinc / Q000737:chemistry*
D000812:Anhydrides; D002264:Carboxylic Acids; D002712:Chlorides; D004952:Esters; D007659:Ketones; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D015032:Zinc; D005459:Fluorides