Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes.
Herein, we report a novel cobalt-catalyzed stereodivergent transfer hydrogenation of alkynes to Z- and E-alkenes. Effective selectivity control is achieved based on a rational catalyst design. Moreover, this mild system allows for the transfer hydrogenation of alkynes bearing a wide range of functional groups in good yields using catalyst loadings as low as 0.2 mol %. The general applicability of this procedure is highlighted by the synthesis of more than 50 alkenes with good chemo- and stereoselectivity. A preliminary mechanistic study revealed that E-alkene product was generated via sequential alkyne hydrogenation to give Z-alkene intermediate, followed by a Z to E alkene isomerization process.
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University , Beijing 100084, China.
Shaomin
S
Fu
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University , Beijing 100084, China.|State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology , Hangzhou 310014, China.
Nan-Yu
NY
Chen
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University , Beijing 100084, China.
Xufang
X
Liu
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University , Beijing 100084, China.
Zhihui
Z
Shao
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology , Hangzhou 310014, China.
Shu-Ping
SP
Luo
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University , Beijing 100084, China.
Qiang
Q
Liu