Release Time:2019-03-12  Hits:

Indexed by: Journal Article

Date of Publication: 2018-07-04

Journal: ADVANCED SYNTHESIS & CATALYSIS

Included Journals: SCIE

Volume: 360

Issue: 13

Page Number: 2429-2434

ISSN: 1615-4150

Key Words: rhodium; regioselectivity; triazolyl-4-phosphonates; internal alkynylphosphonates; mild conditions

Abstract: A regioselective method to access fully substituted 1,2,3-triazolyl-4-phosphonates from the internal alkynylphosphonates by rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) under mild conditions is reported. This approach is water and air compatible and has a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. Fully substituted 1,2,3-triazolyl-4-phosphonates are directly prepared from the internal alkynylphosphonates by RhAAC with high 1,4-regioselectivities. The gram-scale preparation, application to carbohydrate synthesis and the solid-phase synthesis of triazolyl-4-phosphonates are highlights of this method.