Copper-catalyzed deaminative alkynylation of secondary amines with alkynes: selectivity switch in the synthesis of diverse propargylamines. Issue 24 (10th November 2021)

• Record Type: Journal Article
• Authors: Hu, Shengyun; Feng, Huangdi; Xi, Hui; Meng, Yuchen; Li, Ming; Huang, Liliang; Huang, Junhai
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 24(2021)
• Page Start: 6992
• Page End: 6997
• Publication Date: 2021-11-10
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01240a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The copper-catalyzed selective deamination and alkynylation of the unsymmetrical secondary amines with terminal alkynes was reported with a broad substrate scope and excellent functional compatibility. Abstract : Transition-metal catalyzed C–N bond activation has become one of the most promising bond cleavage and formation methods in organic synthesis. This method is still challenging when precise control over the selected C–N bond cleavage between two different C(sp 3 )–N bonds in one molecule is required. Herein, we report a time-dependent selective synthesis of two kinds of the propargylamines using the same CuBr2 /TBHP catalysis system. Control over the addition of terminal alkynes at different reaction times is essential for the site-selective deamination/alkynylation of secondary amines to obtain the corresponding products in good to excellent yields.