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Microwave assisted and in-situ generated palladium nanoparticles catalysed desulfitative synthesis of cross-biphenyls from arylsulfonyl chlorides and phenylboronic acids
Results in Chemistry Pub Date : 2021-08-25 , DOI: 10.1016/j.rechem.2021.100181
Prasanta Kumar Raul 1, 2 , Abhijit Mahanta 1 , Raju K. Borah 1 , Utpal Bora 1 , Ashim Jyoti Thakur 1 , Jyri-Pekka Mikkola 3, 4 , Andrey Shchukarev 3
Affiliation  

A microwave assisted reaction protocol for Suzuki–Miyaura cross-coupling has been developed. Substituted arylboronic acids and arylsulfonyl chlorides coupled under microwave irradiation (MWI) to produce cross-biphenyls in high yields under aerobic condition. The principal advantage of this protocol is that formation of cross-biphenyls was achieved within shorter time along with desulfurization of arylsulfonyl chloride. In-situ generated Pd nanoparticles (NPs) act as catalyst in the reaction. Substituents like methyl, halogens, cyano, amino and t-butyl groups in arylboronic acids tolerate the reaction condition. Pd NPs could be reused several times under chosen reaction conditions without losing its activity significantly. The product formation and the role of the catalyst for the cross-coupling reaction has been rationalised with the help of a proposed mechanism. This reaction is one of the examples of In-situ generated Nanoparticles-catalyzed Organic Synthesis Enhancement (i-NOSE) approach. The approach derives its importance in terms of catalyst’s (i) simple preparation method, (ii) stability under the chosen reaction condition, (iii) substrate specificity, (iv) simple filtration to recover the catalyst and (v) easy regeneracy which clearly indicate that the approach could be applicable for various types of catalytic transformations.



中文翻译:

微波辅助和原位生成的钯纳米粒子催化芳基磺酰氯和苯基硼酸脱硫合成交叉联苯

已经开发了 Suzuki-Miyaura 交叉偶联的微波辅助反应方案。取代的芳基硼酸和芳基磺酰氯在微波辐射 (MWI) 下偶联,在有氧条件下以高产率生产交叉联苯。该协议的主要优点是,随着芳基磺酰氯的脱硫,可以在更短的时间内形成交叉联苯。原位生成的 Pd 纳米粒子 (NPs) 在反应中充当催化剂。芳基硼酸中的甲基、卤素、氰基、氨基和叔丁基等取代基可以耐受反应条件。Pd NPs 可以在选定的反应条件下重复使用多次而不会显着降低其活性。在提出的机制的帮助下,产物的形成和催化剂在交叉偶联反应中的作用已经合理化。该反应是原位反应的例子之一生成纳米粒子催化有机合成增强 (i-NOSE) 方法。该方法的重要性体现在催化剂的 (i) 简单的制备方法、(ii) 在所选反应条件下的稳定性、(iii) 底物特异性、(iv) 简单过滤以回收催化剂和 (v) 容易再生,这清楚地表明该方法可适用于各种类型的催化转化。

更新日期:2021-08-30
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