2725-60-2Relevant academic research and scientific papers
Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
Dar'In, Dmitry,Kantin, Grigory,Bakulina, Olga,Krasavin, Mikhail
, p. 2259 - 2266 (2020)
A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.
A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis
Dar'In, Dmitry,Kantin, Grigory,Krasavin, Mikhail
supporting information, p. 5239 - 5242 (2019/05/08)
Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.
Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
Wu, Youzhi,Sun, Peng,Zhang, Kaifan,Yang, Tie,Yao, Hequan,Lin, Aijun
, p. 2166 - 2173 (2016/03/15)
Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.
Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds
Chen, Xun,Xie, Ying,Xiao, Xinsheng,Li, Guoqiang,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 15328 - 15331 (2015/10/20)
A Rh(iii)-catalyzed cross-coupling/cyclization cascade of α-imino Csp3-H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp3-H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
Rhodium carbene routes to oxazoles and thiazoles. Catalyst effects in the synthesis of oxazole and thiazole carboxylates, phosphonates, and sulfones
Shi, Baolu,Blake, Alexander J.,Lewis, William,Campbell, Ian B.,Judkins, Brian D.,Moody, Christopher J.
supporting information; experimental part, p. 152 - 161 (2010/04/04)
(Chemical Equation Presented) Dirhodium tetraacetate catalyzed reaction of α-diazo-β-keto-carboxylates and -phosphonates with arenecarboxamides gives 2-aryloxazole-4-carboxylates and 4-phosphonates by carbene N-H insertion and cyclodehydration. In stark contrast, dirhodium tetrakis(heptafluorobutyramide) catalysis results in a dramatic change of regioselectivity to give oxazole-5-carboxylates and 5-phosphonates. α-Diazo-β-ketosulfones behave similarly and give 5-sulfonyloxazoles upon dirhodium tetrakis-(heptafluorobutyramide) catalyzed reaction with carboxamides. The analogous reactions of thiocarboxamides give the corresponding thiazole-5-carboxylates, -phosphonates, and -sulfones. 2009 American Chemical Society.
