A carrier-free and recyclable protocol for the cross-coupling of terminal alkynes with arylboronic acids in H2O/TBAB. Issue 30 (25th July 2019)

• Record Type: Journal Article
• Authors: Tang, Bo-Xiao; Kuang, Ren-Yun; Wen, Ji-Wu; Huang, Xiang; Zhang, Zhen-Xing; Shen, Yu-Jun; Chen, Jia-Ping; Wu, Wen-Ying
• Is Part Of: Tetrahedron letters. Volume 60:Issue 30(2019)
• Page Start: 1975
• Page End: 1977
• Publication Date: 2019-07-25
• Subjects: Reusability -- Carrier-free -- H2O/TBAB -- Sonogashira-type coupling; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.06.047
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Ligand-free, recyclable and unsupported Sonogashira-type coupling systems is demonstrated. The whole systems can be recovered and used for 3 cycles directly. Performing the reactions in water/ionic liquid makes this methodology greener. Abstract: A new and recyclable protocol was developed for Pd(OAc)2 -catalyzed the cross-coupling reaction of terminal alkynes with arylboronic acids using environmentally friendly H2 O/TBAB as reaction medium. A series of cross-coupling products containing internal acetylenic bond can be obtained with good selectivity and yield. The Pd(OAc)2 /H2 O/TBAB system was stable in the Sonogashira-type cross-coupling reaction and could be used at least three cycles without considerable decrease in catalytic performance. The results suggest that the unsupported and recyclable systems can be extended to the other realm of CC bond formation in synthetic organic chemistry.