Tetrabutylammonium Bromide (TBAB)-Promoted, Pd/Cu-Catalyzed Sonogashira Coupling of -Tosyl Aryltriazenes.

Org Lett

School of Chemistry & Molecular Engineering, East China University of Science & Technology, 130 Meilong Rd, Shanghai 200237, China.

Published: May 2024

Sonogashira coupling of -tosyl aryltriazenes is reported to offer arylalkynes in yields up to 92% with the aid of tetrabutylammonium bromide (TBAB) as a dual activator for both the palladium catalyst and aryltriazenes. Common functional groups could be well tolerated, although large electronic effects from alkynes were observed. TBAB-assisted oxidative addition of palladium(0) to aryltriazene instead of in situ formed arylhalide has been proposed to initiate the catalytic cycle.

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http://dx.doi.org/10.1021/acs.orglett.4c01565DOI Listing

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