TY - JOUR
T1 - Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones
T2 - Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones
AU - He, Zhen
AU - Qi, Xiaotian
AU - She, Zhijie
AU - Zhao, Yinsong
AU - Li, Shiqing
AU - Tang, Junbin
AU - Gao, Ge
AU - Lan, Yu
AU - You, Jingsong
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/2/3
Y1 - 2017/2/3
N2 - A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.
AB - A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.
UR - https://www.scopus.com/pages/publications/85011371069
U2 - 10.1021/acs.joc.6b02575
DO - 10.1021/acs.joc.6b02575
M3 - 文章
C2 - 28051318
AN - SCOPUS:85011371069
SN - 0022-3263
VL - 82
SP - 1403
EP - 1411
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -