Zinc(II)‐Catalyzed Synthesis of Propargylamines by Coupling Aldimines and Ketimines with Alkynes. Issue 1 (3rd January 2018)

• Record Type: Journal Article
• Authors: Shehzadi, Syeda Aaliya; Saeed, Aamer; Lemière, Filip; Maes, Bert U. W.; Abbaspour Tehrani, Kourosch
• Is Part Of: European journal of organic chemistry. Issue 1(2018)
• Page Start: 78
• Page End: 88
• Publication Date: 2018-01-03
• Subjects: C‐C coupling -- Alkynes -- Amines -- Schiff bases -- Zinc; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701567
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A Zn II ‐catalyzed reaction between imines, which were derived from unactivated aldehydes or ketones and primary amines or α‐amino acid esters, and terminal alkynes has led to the rapid and efficient formation of tri‐ and tetrasubstituted propargylamines (from aldimines and ketimines, respectively) in good to excellent yields. No additives or extra Lewis acid reagents were required for the imine‐alkyne coupling reaction. Abstract : Imines derived from unactivated aldehydes or ketones and primary amines or α‐amino acid esters have been shown to undergo a Zn II ‐catalyzed reaction with a variety of terminal alkynes to give secondary propargylamines that have tri‐ and tetrasubstituted α‐carbon atoms (from aldimines and ketimines, respectively).