Enantioselective cross dehydrogenative coupling reaction catalyzed by Rose Bengal incorporated-Cu(I)-dimeric chiral complexes

A novel dimeric chiral Cu(I) amino alcohol based in-situ generated catalyst in combination with Rose Bengal as a photo-redox catalyst were used for the first time for asymmetric cross dehydrogenative coupling of N-aryl tetrahydroisoquinoline with terminal alkynes enroute for propargylic amines synth...

Full description

Saved in:
Bibliographic Details
Published in:Catalysis communications 2017-08, Vol.99, p.94-99
Main Authors: Kumar, Gaurav, Verma, Shailesh, Ansari, Amamudin, Khan, Noor-ul H., Kureshy, Rukhsana I.
Format: Article
Language:English
Subjects:
Alkynylation
Cross dehydrogenative coupling
Photo redox
Schiff bases
Tetrahydroisoquinoline
Visible light
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel dimeric chiral Cu(I) amino alcohol based in-situ generated catalyst in combination with Rose Bengal as a photo-redox catalyst were used for the first time for asymmetric cross dehydrogenative coupling of N-aryl tetrahydroisoquinoline with terminal alkynes enroute for propargylic amines synthesis using molecular oxygen as a terminal oxidant. This methodology provides an atom economical and green way to access diversified optically active alkynylation product selectively at C1-position of N-aryl tetrahydroisoquinoline under moderate conditions with high enantioselectivity (up to 99%) and excellent yield (up to 90%). [Display omitted] •First asymmetric CDC reaction using Rose Bengal with Cu(I) chiral complexes.•This protocol used for the synthesis of optically active propargylic amines.•Excellent catalytic activity in terms of enantioselectivity and product yields.•Synthesis of chiral Schiff base ligands using different amino alcohols.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2017.05.026