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Tetrabutylammonium Bromide (TBAB)-Promoted, Pd/Cu-Catalyzed Sonogashira Coupling of N-Tosyl Aryltriazenes
Organic Letters ( IF 4.9 ) Pub Date : 2024-05-22 , DOI: 10.1021/acs.orglett.4c01565
Jun Cao 1 , Wenbin Ding 1 , Gang Zou 1
Organic Letters ( IF 4.9 ) Pub Date : 2024-05-22 , DOI: 10.1021/acs.orglett.4c01565
Jun Cao 1 , Wenbin Ding 1 , Gang Zou 1
Affiliation
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Sonogashira coupling of N-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.
中文翻译:
四丁基溴化铵 (TBAB) 促进、Pd/Cu 催化的 N-甲苯磺酰基芳基三氮烯的 Sonogashira 偶联
据报道,借助四丁基溴化铵 (TBAB) 作为钯催化剂和芳基三氮烯的双重活化剂, N-甲苯磺酰基芳基三氮烯的 Sonogashira 偶联可提供高达 92% 的芳基炔烃。尽管观察到来自炔烃的大电子效应,但常见的官能团具有良好的耐受性。已提出通过 TBAB 辅助将钯 (0) 氧化加成至芳基三氮烯而不是原位形成的芳基卤来启动催化循环。
更新日期:2024-05-22
中文翻译:

四丁基溴化铵 (TBAB) 促进、Pd/Cu 催化的 N-甲苯磺酰基芳基三氮烯的 Sonogashira 偶联
据报道,借助四丁基溴化铵 (TBAB) 作为钯催化剂和芳基三氮烯的双重活化剂, N-甲苯磺酰基芳基三氮烯的 Sonogashira 偶联可提供高达 92% 的芳基炔烃。尽管观察到来自炔烃的大电子效应,但常见的官能团具有良好的耐受性。已提出通过 TBAB 辅助将钯 (0) 氧化加成至芳基三氮烯而不是原位形成的芳基卤来启动催化循环。