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Relevant academic research and scientific papers

Chemoselective Nitrosylation of Anilines and Alkynes via Fragmentary or Complete NO Incorporation

The cycloaddition reactions have been explored extensively and provided an efficient strategy for the synthesis of cyclic compounds. Traditionally, the reaction partners were in extenso incorporated into the cyclic products without fragmentation. From a different perspective, if certain fragmentations via chemical-bond cleavage are involved in this cycloaddition reaction, it would change the assembly sequence and enable more product diversity. Here, we report a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation. The formation of multiple C–N bonds, an unexpected C–N bond, and N=O bond cleavage make this fragmentary cycloaddition reaction an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides or quinoxaline N-oxides. Facile operation in open-air, metal-free, and mild conditions renders this protocol particularly practical and attractive. A series of mechanistic studies and density functional theory calculations were also conducted, which help to explain the fragmentary or complete NO incorporation processes, broadening the field of new reaction discovery. Exploring novel structures and developing convenient and direct methods to achieve them are an essential issue in synthetic chemistry. In traditional cycloaddition reactions, the reaction partners are in extenso incorporated into the cyclic compound products. In contrast, the fragmentary incorporation of the reaction partners via chemical-bond cleavage in cycloaddition reactions would change the assembly sequence and enable more product diversity. However, fragmentary incorporation in cycloaddition reactions remains a challenging issue because of the high bond-dissociation energy and poor selectivity. This paper reports a fragmentary cycloaddition reaction that enables a series of new structures through a controllable radical process. This work also reveals the diversity of transformation of free radical intermediates. The accessible products might also trigger some interest in pharmaceutical science and materials science. Cycloaddition reactions provide an efficient strategy for the synthesis of cyclic compounds and have been well developed. However, cycloaddition reactions with fragmentary partner incorporation via the cleavage of multiple bonds, which allows for more structural diversity than traditional cycloaddition reactions, have seldom been reported. Here, we describe a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation for an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides, or quinoxaline N-oxides.

A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water

The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol