Title of Paper:Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) of Internal Alkynylphosphonates with High Regioselectivities under Mild Conditions

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Date of Publication:2018-07-04

Journal:ADVANCED SYNTHESIS & CATALYSIS

Included Journals:SCIE

Volume:360

Issue:13

Page Number:2429-2434

ISSN No.: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.