Nickel-catalyzed reductive Heck type coupling of saturated alkyl halides with acrylates and oxabenzonorbornadiene

作者：Shukla Paritosh^*; Sharma Ashok; Pallavi Badvel; Cheng Chien Hong

来源：Tetrahedron, 2015, 71(15): 2260-2266.

DOI：10.1016/j.tet.2015.02.067

• Reductive coupling
• Heck reaction
• Nickel catalyst
• Oxabenzonorbornadiene

The Heck reaction is a well-established transition-metal catalyzed reaction for coupling alkenes with sp(2) alkyl halides to give novel unsaturated compounds. Herein we report an analogous Heck-inspired, simple efficient coupling of sp(3) alkyl halides with electron-withdrawing alkenes to form reductive coupling products where saturated esters are obtained. A range of acrylates were coupled with sp3 alkyl halides in the presence of Ni(PPh3)(2)C-12 catalyst, Zn metal powder, CH3CN solvent, and water, at 80 degrees C to form the reductive Heck type saturated ester products in good yields. This strategy was further extended to couple oxabenzonorbornadiene with the alkyl halides resulting in ring opening to give rise to bicyclic alcohol products. The mechanism for both the reactions appears to be the usual oxidative-addition driven alkene insertion reaction where the water appears to act as the protonating agent.

• 出版日期2015-4-15
• 单位清华大学