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Journal ArticleDOI

Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)2–H Coupling

28 Aug 2022-Molecules-Vol. 27, Iss: 17, pp 5539-5539
TL;DR: In this paper , an S(O)2-N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis was developed.
Abstract: We here have developed an S(O)2–N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet nitrene and followed coupling with sulfonyl radicals in situ to achieve structurally diverse benzenesulfinamides in good yields.

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References
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Journal ArticleDOI
20 Jun 2018-Nature
TL;DR: The synergistic combination of copper catalysis and photoredox catalysis forms sp3 C–N bonds in a rapid, room-temperature coupling protocol with high efficiencies and regioselectivities and a broad substrate scope, enabling the rapid construction of molecular complexity and the late-stage functionalization of bioactive pharmaceuticals.
Abstract: Over the past three decades, considerable progress has been made in the development of methods to construct sp2 carbon-nitrogen (C-N) bonds using palladium, copper or nickel catalysis1,2. However, the incorporation of alkyl substrates to form sp3 C-N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge. This cross-coupling system uses naturally abundant alkyl carboxylic acids and commercially available nitrogen nucleophiles as coupling partners. It is applicable to a wide variety of primary, secondary and tertiary alkyl carboxylic acids (through iodonium activation), as well as a vast array of nitrogen nucleophiles: nitrogen heterocycles, amides, sulfonamides and anilines can undergo C-N coupling to provide N-alkyl products in good to excellent efficiency, at room temperature and on short timescales (five minutes to one hour). We demonstrate that this C-N coupling protocol proceeds with high regioselectivity using substrates that contain several amine groups, and can also be applied to complex drug molecules, enabling the rapid construction of molecular complexity and the late-stage functionalization of bioactive pharmaceuticals.

218 citations

Journal ArticleDOI
TL;DR: In this article, a novel, rapid, and environmentally-friendly protocol for the synthesis of sulfonamides using iodine as catalyst under solvent-free conditions is described, which involves the oxidative coupling of sulfonyl hydrazides and amines in the presence of catalytic amount of iodine using TBHP as oxidant.

38 citations

Journal ArticleDOI
TL;DR: Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate inalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic Aziridines.

36 citations

Journal ArticleDOI
TL;DR: In this article, a double sulfinylation/hydrolysis strategy was used for the selective synthesis of monoprotected N-sulfinyl amino alcohols through double sulfinamides.

33 citations

Journal ArticleDOI
TL;DR: A photoredox strategy for the synthesis of a wide range of allylic amines and ethers from carboxylic acids and alkynes has been developed in this paper, which relies on the perturbation of the ground-sta...
Abstract: A photoredox strategy for the synthesis of a wide range of allylic amines and ethers from carboxylic acids and alkynes has been developed. This approach relies on the perturbation of the ground-sta...

30 citations