TY - JOUR
T1 - Organophotocatalyzed E and Z stereoselective Csp3-Csp2 bond forming cross coupling reactions of carboxylic acids with β-aryl-vinyl halides
AU - Huang, He
AU - Zhang, Yueteng
AU - Ji, Peng
AU - Mariano, Patrick S.
AU - Wang, Wei
N1 - Publisher Copyright:
© 2020 The Authors
PY - 2021/2
Y1 - 2021/2
N2 - Owing to their importance in organic synthesis, transition metal catalyzed cross-coupling reactions have been the focus of many studies. Recently, it was recognized that merged transition metal and photoredox catalysis is a powerful strategy for the design of challenging Csp3-Csp2 bond forming cross coupling reactions. However, these reactions require metals (e.g., Ni) to activate Csp2-halogen bonds. In the current investigation, we developed a new, photocatalysis based, metal free approach to accomplish Csp3-Csp2 bond formation between an alkyl fragment, derived from a carboxylic acid, and a vinyl moiety of a,β-aryl-substituted vinyl halide. The cross coupling process, which is activated by using the simple organic dye 4CzIPN, acting as a single electron transfer type photocatalyst, and visible light, is chemoselective, E-stereoselective and efficient. Moreover, upon prolonged irradiation of the reaction mixture, 4CzIPN serving as an energy transfer photocatalyst, promotes isomerization of the initially formed alkenes into mixtures enriched in the Z-isomers.
AB - Owing to their importance in organic synthesis, transition metal catalyzed cross-coupling reactions have been the focus of many studies. Recently, it was recognized that merged transition metal and photoredox catalysis is a powerful strategy for the design of challenging Csp3-Csp2 bond forming cross coupling reactions. However, these reactions require metals (e.g., Ni) to activate Csp2-halogen bonds. In the current investigation, we developed a new, photocatalysis based, metal free approach to accomplish Csp3-Csp2 bond formation between an alkyl fragment, derived from a carboxylic acid, and a vinyl moiety of a,β-aryl-substituted vinyl halide. The cross coupling process, which is activated by using the simple organic dye 4CzIPN, acting as a single electron transfer type photocatalyst, and visible light, is chemoselective, E-stereoselective and efficient. Moreover, upon prolonged irradiation of the reaction mixture, 4CzIPN serving as an energy transfer photocatalyst, promotes isomerization of the initially formed alkenes into mixtures enriched in the Z-isomers.
KW - Cross-coupling reaction
KW - Organocatalysis
KW - Photochemistry
KW - Photoredox
KW - Synthetic methods
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U2 - 10.1016/j.gresc.2020.11.002
DO - 10.1016/j.gresc.2020.11.002
M3 - Article
AN - SCOPUS:85114013275
SN - 2666-5549
VL - 2
SP - 27
EP - 31
JO - Green Synthesis and Catalysis
JF - Green Synthesis and Catalysis
IS - 1
ER -