The trans-hydroboration of alkyne represents a challenging task in organic synthesis.Reported herein is an Et2 Zn promotedβ-trans hydroboration of ynamides by using N-heterocyclic carbene(NHC)-ligated borane as boryl...The trans-hydroboration of alkyne represents a challenging task in organic synthesis.Reported herein is an Et2 Zn promotedβ-trans hydroboration of ynamides by using N-heterocyclic carbene(NHC)-ligated borane as boryl source.The reaction leads to a stereoselective construction of enamides bearing a valuable boryl substituent.Both aromatic and aliphatic ynamides were applicable to the reaction.Synthetic transformation of the C-B bond in the product via Suzuki-Miyaura coupling provides a simple and stereospecific route to multi-substituted enamides.Mechanistic studies were conducted and the possible mechanism was discussed.展开更多
基金Financial supports from the Key Project of Chinese National Programs for Fundamental Research and Development(No.2016YFA0602900)the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(No.2017BT01Y093)+1 种基金the Natural Science Foundation of China(No.81873071)the Pearl River S&T Nova Program of Guangzhou(No.201906010059)are gratefully acknowledged。
文摘The trans-hydroboration of alkyne represents a challenging task in organic synthesis.Reported herein is an Et2 Zn promotedβ-trans hydroboration of ynamides by using N-heterocyclic carbene(NHC)-ligated borane as boryl source.The reaction leads to a stereoselective construction of enamides bearing a valuable boryl substituent.Both aromatic and aliphatic ynamides were applicable to the reaction.Synthetic transformation of the C-B bond in the product via Suzuki-Miyaura coupling provides a simple and stereospecific route to multi-substituted enamides.Mechanistic studies were conducted and the possible mechanism was discussed.
