Copper-Catalyzed Formal Transfer Hydrogenation/Deuteration of Aryl Alkynes

Authors

Samantha E. Sloane, Marquette University
Albert Reyes, Marquette University
Zoua Pa Vang, Marquette University
Lingzi Li, Marquette University
Kiera T. Behlow, Marquette University
Joseph R. Clark, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

11-10-2020

Publisher

American Chemical Society

Source Publication

Organic Letters

Source ISSN

1523-7060

Abstract

A copper-catalyzed reduction of alkynes to alkanes and deuterated alkanes is described under transfer hydrogenation and transfer deuteration conditions. Commercially available alcohols and silanes are used interchangeably with their deuterated analogues as the hydrogen or deuterium sources. Transfer deuteration of terminal and internal aryl alkynes occurs with high levels of deuterium incorporation. Alkyne-containing complex natural product analogues undergo transfer hydrogenation and transfer deuteration selectively, in high yield. Mechanistic experiments support the reaction occurring through a cis-alkene intermediate and demonstrate the possibility for a regioselective alkyne transfer hydrodeuteration reaction.

Comments

Accepted version. Organic Letters, Vol. 22, No. 22 (November 10, 2020): 9139-9144. DOI. © 2020 American Chemical Society. Used with permission.

Recommended Citation

Sloane, Samantha E.; Reyes, Albert; Vang, Zoua Pa; Li, Lingzi; Behlow, Kiera T.; and Clark, Joseph R., "Copper-Catalyzed Formal Transfer Hydrogenation/Deuteration of Aryl Alkynes" (2020). Chemistry Faculty Research and Publications. 1017.
https://epublications.marquette.edu/chem_fac/1017