Palladium-Catalyzed Selective Syntheses of 2, 3-Allenyl Amines via Double Functionalization Coupling of 2-Alkynyl-1, 4-diol Dicarbonates

Zhengnan Zhou; Can Li; Shengming Ma

doi:10.1002/cjoc.202400298

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (19) : 2357 -2362. DOI: 10.1002/cjoc.202400298

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Palladium-Catalyzed Selective Syntheses of 2, 3-Allenyl Amines via Double Functionalization Coupling of 2-Alkynyl-1, 4-diol Dicarbonates

Zhengnan Zhou ¹^,²
, Can Li ¹^,²
, Shengming Ma ¹^,³^,^†

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Abstract

2, 3-Allenyl amines have shown wide applicability in biomedical and synthetic applications. Due to their enormous potential for applications, researchers have been dedicated to the development of methods for synthesizing 2, 3-allenyl amines. Herein, a palladium-catalyzed three-component reaction of 2-alkynyl-1, 4-diol dicarbonates, organoboronic acids, and nitrogen nucleophiles forming 2, 3-allenyl amines with excellent regio- and chemo-selectivity has been developed. Substrate compatibility and synthetic applications have been demonstrated. Control experiments supported a mechanism involving 1, 2, 3-triene-Pd species and methylene-π-allyl palladium species.

Keywords

Pd catalysis / 2, 3-Allenyl amine / Alk-2-yn-1, 4-diol dicarbonate / Organoboronic acid / 1, 2, 3-Triene / Methylene-π-allyl palladium species / Regioselectivity / Chemoselectivity

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Zhengnan Zhou, Can Li, Shengming Ma. Palladium-Catalyzed Selective Syntheses of 2, 3-Allenyl Amines via Double Functionalization Coupling of 2-Alkynyl-1, 4-diol Dicarbonates. Chinese Journal of Chemistry, 2024, 42(19): 2357-2362 DOI:10.1002/cjoc.202400298