Synthesis 2020; 52(16): 2379-2386
DOI: 10.1055/s-0040-1707395
paper
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Partial Hydrogenation of Activated Alkynes Mediated by Triphenylphosphine

Ana Patricia Cocoletzi-Xochitiotzi
a  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México   Email: [email protected]
b  Universidad Autónoma de Tlaxcala, Facultad de Ciencias Básicas, Ingeniería y Tecnología, Calzada Apizaquito S/N 90300, Apizaco, Tlaxclala, México
,
Miguel Hernández-Hernández
a  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México   Email: [email protected]
b  Universidad Autónoma de Tlaxcala, Facultad de Ciencias Básicas, Ingeniería y Tecnología, Calzada Apizaquito S/N 90300, Apizaco, Tlaxclala, México
,
Ignacio Medina-Mercado
a  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México   Email: [email protected]
,
Williams de Jesús Jiménez-Martínez
a  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México   Email: [email protected]
,
Virginia Maricela Mastranzo
a  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México   Email: [email protected]
b  Universidad Autónoma de Tlaxcala, Facultad de Ciencias Básicas, Ingeniería y Tecnología, Calzada Apizaquito S/N 90300, Apizaco, Tlaxclala, México
,
a  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México   Email: [email protected]
› Author Affiliations
This work was supported by CONACyT (A1-S-7805) and DGAPA (IN202017).
Further Information

Publication History

Received: 15 March 2020

Accepted after revision: 08 April 2020

Publication Date:
12 May 2020 (online)


Abstract

Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z-isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.

Supporting Information

 
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