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苯并噻唑亚磺酸盐:一种在无氧化条件下的亚磺酸转移试剂。

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions.

机构信息

Department of Chemistry, Washington State University , Pullman, Washington 99164, United States.

出版信息

Org Lett. 2017 Jul 21;19(14):3819-3822. doi: 10.1021/acs.orglett.7b01693. Epub 2017 Jul 3.

DOI:10.1021/acs.orglett.7b01693
PMID:28670905
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5863730/
Abstract

Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.

摘要

亚磺酸是天然产物合成和药物化学中常见的中间体。然而,由于其高反应性、不稳定性和苛刻的反应条件,它们很难合成。在此,我们开发了一种无需氧化的方法,使用 2-亚磺酰基苯并噻唑 (BTS) 来制备亚磺酸和亚磺酸盐。我们还通过一锅法合成砜和磺酰胺证明了其合成用途。

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本文引用的文献

1
One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.钯催化一锅法由芳基溴化物合成磺酰氟
Chem Sci. 2017 Feb 1;8(2):1233-1237. doi: 10.1039/c6sc03924c. Epub 2016 Oct 11.
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Selective degradation of splicing factor CAPERα by anticancer sulfonamides.抗癌磺胺类药物选择性降解剪接因子 CAPERα。
Nat Chem Biol. 2017 Jun;13(6):675-680. doi: 10.1038/nchembio.2363. Epub 2017 Apr 24.
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Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates.亚磺酸盐阴离子合成砜和砜酰胺:重新审视硫代磺酸盐的实用性。
J Org Chem. 2017 Feb 3;82(3):1761-1767. doi: 10.1021/acs.joc.6b03016. Epub 2017 Jan 25.
4
A General, One-Pot Method for the Synthesis of Sulfinic Acids from Methyl Sulfones.由甲基砜合成磺酸的通用一锅法。
Org Lett. 2016 Dec 2;18(23):5994-5997. doi: 10.1021/acs.orglett.6b02723. Epub 2016 Nov 14.
5
Reaction of Alkyl Halides with Rongalite: One-Pot and Telescoped Syntheses of Aliphatic Sulfonamides, Sulfonyl Fluorides, and Unsymmetrical Sulfones.卤代烷与吊白块的反应:脂肪族磺酰胺、磺酰氟和不对称砜的一锅法和缩合合成。
Org Lett. 2016 Nov 18;18(22):5848-5851. doi: 10.1021/acs.orglett.6b02894. Epub 2016 Oct 27.
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J Am Chem Soc. 2016 Jun 15;138(23):7353-64. doi: 10.1021/jacs.6b02960. Epub 2016 Jun 2.
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ACS Chem Biol. 2016 Jun 17;11(6):1647-51. doi: 10.1021/acschembio.6b00106. Epub 2016 Apr 7.
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Angew Chem Int Ed Engl. 2016 Jan 11;55(2):747-50. doi: 10.1002/anie.201508370. Epub 2015 Nov 24.
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Palladium-Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids, Unactivated Alkyl Halides, and Potassium Metabisulfite.钯催化的(杂)芳基硼酸、未活化的烷基卤化物和重亚硫酸钾合成(杂)芳基烷基砜。
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10
Combining organometallic reagents, the sulfur dioxide surrogate DABSO, and amines: a one-pot preparation of sulfonamides, amenable to array synthesis.结合有机金属试剂、二氧化硫替代物DABSO和胺类:一种适用于阵列合成的磺酰胺一锅法制备。
Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1168-71. doi: 10.1002/anie.201409283. Epub 2014 Nov 27.