Work

Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction

Year: 2016

Type: article

Abstract: The Nicholas reaction has been applied to the installation of alkyne ligation handles. Acid-promoted propargylation of hydroxyl, sulfhydryl, amino, and carboxyl groups using dicobalt hexacarbonyl-stabilized propargylium ions is reported. This method is useful for introduction of propargyl groups into base-sensitive molecules, thereby expanding the toolbox of methods for the incorporation of alkynes for bio-orthogonal reactions. High-value molecules are used as the limiting reagent, and various propargylium ion precursors are compared.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6b02088

Authors: Sarah M. Wells, John C. Widen, Daniel A. Harki, Kay M. Brummond

Institutions: University of Pittsburgh, University of Minnesota

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: U.S. Department of Defense, National Cancer Institute, National Institute of General Medical Sciences

Awards: Allenic [2 + 2 + 1] Reactions Enabling Syntheses of Natural Products with 7-Membe, CHEMOPROTEOMICS PROFILING OF PARTHENOLIDE IN HUMAN GLIOBLASTOMA, G7214754510, Cancer Center Support Grant