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Nickel(II)/N‐Heterocyclic Carbene Catalyzed Desulfinylative Arylation by C−S Cleavage of Aryl Sulfoxides with Phenylboronic Acids
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-06-29 , DOI: 10.1002/adsc.202000531
Xiaowen Yi 1, 2 , Kai Chen 1 , Junjun Guo 1 , Wei Chen 1 , Wanzhi Chen 1
Affiliation  

Suzuki‐Miyaura coupling of haloarenes is the most widely used protocol for the synthesis of biphenyls. Organosulfur compounds are promising electrophiles since they are abundant in nature and versatile in organic synthesis. We report here the desulfinylative Suzuki‐Miyaura coupling of aryl sulfoxides with phenylboronic acids using bench‐stable nickel/5‐(2,4,6‐triisopropylphenyl)imidazolylidene[1,5‐a]pyridines as the catalyst. The ligands are readily prepared from common commercial chemicals. The method is applicable to both symmetric and unsymmetric aryl sulfoxides, and a range of biphenyls bearing various functional groups were obtained in up to 94% yield.

中文翻译:

镍(II)/ N-杂环碳烯通过芳基亚砜与苯基硼酸的CS裂解催化脱硫酰基化

卤代芳烃的Suzuki-Miyaura偶联是联苯合成中使用最广泛的方案。有机硫化合物是有前途的亲电子试剂,因为它们性质丰富且有机合成用途广泛。我们在此报告使用稳定的镍/ 5-(2,4,6-三异丙基苯基)咪唑基亚甲基[1,5- a ]吡啶作为催化剂将芳基亚砜与苯基硼酸的脱亚磺酰基铃木-宫浦偶合。配体易于从常见的商业化学品制备。该方法适用于对称和不对称的芳基亚砜,并且以高达94%的收率获得了一系列带有各种官能团的联苯。
更新日期:2020-06-29
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