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钯催化亚砜酯与芳基和烯基硼酸的磺酰化反应。

Palladium-Catalyzed Sulfinylation of Aryl- and Alkenylborons with Sulfinate Esters.

机构信息

Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.

Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo, 125-8585, Japan.

出版信息

Org Lett. 2021 May 7;23(9):3793-3797. doi: 10.1021/acs.orglett.1c01292. Epub 2021 Apr 28.

DOI:10.1021/acs.orglett.1c01292
PMID:33908784
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8289295/
Abstract

An efficient, direct sulfinylation of organoborons catalyzed by palladium is disclosed. Treatment of organoborons and sulfinate esters in the presence of a palladium precatalyst provided a broad range of sulfoxides. Various organosulfur compounds having oxidizable functional groups were successfully prepared through the sulfoxide synthesis.

摘要

本文公开了一种钯催化的高效、直接的有机硼砜化反应。在钯前催化剂的存在下，将有机硼和亚磺酸盐酯处理，提供了广泛的砜。通过砜的合成，成功制备了具有可氧化官能团的各种有机硫化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/f3374c305ea7/ol1c01292_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/03643a69bceb/ol1c01292_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/ec2d54cf1ef8/ol1c01292_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/fd2fa85b7904/ol1c01292_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/f3374c305ea7/ol1c01292_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/03643a69bceb/ol1c01292_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/ec2d54cf1ef8/ol1c01292_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/fd2fa85b7904/ol1c01292_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f52f/8289295/f3374c305ea7/ol1c01292_0004.jpg

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本文引用的文献

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Chem Soc Rev. 2020 May 27. doi: 10.1039/c9cs00837c.
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Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions.亚砜的亚砜酯在类似 Pummerer 条件下的合成。
Chem Commun (Camb). 2020 May 19;56(40):5429-5432. doi: 10.1039/d0cc02253e.
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Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts.钯催化芳基溴化物与（杂）芳基亚磺酸盐的脱硫交叉偶联反应的机理研究。
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Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide.甲磺酸二甲酯与卤代苄的甲磺酰化反应。
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Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.硫（IV）的成键和断键反应：亚砜、锍盐、叶立德和亚磺酸盐。
Chem Rev. 2019 Jul 24;119(14):8701-8780. doi: 10.1021/acs.chemrev.9b00111. Epub 2019 Jun 25.
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Synthesis of Alkynyl Sulfides by Copper-Catalyzed Thiolation of Terminal Alkynes Using Thiosulfonates.通过铜催化硫代磺酸酯对末端炔烃进行硫醇化反应合成炔基硫醚
Org Lett. 2019 May 3;21(9):3172-3177. doi: 10.1021/acs.orglett.9b00875. Epub 2019 Apr 19.
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