Continuous flow as a benign strategy for the synthesis of Thioesters via selective C-N bond cleavage
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Continuous flow as a benign strategy for the synthesis of Thioesters via selective C-N bond cleavage Mohanraj Kandasamy 1 & Antolin Jesila Jesu Amalraj 1 & Gopi Perumal 1 & Balaji Ganesan 1 & Gopal Chandru Senadi 2 & Wei-Yu Lin 1,3,4 Received: 6 February 2020 / Accepted: 10 March 2020 # Akadémiai Kiadó 2020
Abstract A metal-free C-N bond cleavage of amide functionality has been reported for the efficient and rapid synthesis of thioester in a simple flow system. The feasibility of this method has been investigated with various aliphatic and aromatic thiols with Nacylamide derivatives to deliver the corresponding thioesters. The fruitful outcome of this process includes good to excellent yields, broad functional group compatibility and can afford the thioesters in just 40 s. Keywords Continuous flow . Thioester . Metal free amide cleavage
Introduction In recent years, amide functionality have been employed as an efficient cross-coupling partner in various organic transformations catalyzed by either transition metal or metal-free reaction conditions. [1–5] In this context, the common transformations that took place in metal-catalyzed reactions are acyl transfer and decarbonylative reactions. [6–10] On the other hand, amide can employed as an acyl transfer agent to synthesize new functional entities such as keto, [11] ester, [12] anhydride [13, 14] and trans-amide reaction [12, 15, 16] under metal-free condition. The main cause for the transformation is due to the twisting nature of N-C bond. In this directions, Garg [17] Electronic supplementary material The online version of this article (https://doi.org/10.1007/s41981-020-00090-w) contains supplementary material, which is available to authorized users. * Wei-Yu Lin [email protected] 1
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Republic of China
2
Department of Chemistry, Faculty of Engineering and Technology, SRM Institute of Science and Technology, Kattankulathur, Chennai -603203, India
3
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan, Republic of China
4
Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Republic of China
and Danoun [18] reported a Ni - and Co- catalyzed esterification reaction using N-methyl-N-phenylbenzamide and N-BocN-phenylbenzamide, respectively. Later, transition metal-free esterification was developed by Zeng [19] and Szostak [12] using N-tosyl-N-phenylbenzamide and N-acyl-glutarimide, respectively. [5] Recently, Cheng and co-workers [20] used amide for thioester synthesis with catalytic amount of potassium carbonate as a base to initiate the thioesterification reaction. Nevertheless, still challenges remain to be solved such as requirement of inert atmosphere, metal catalyst, high reaction temperature, tedious reaction procedure for preparation of starting material and longer reaction time. Thioesters are known to possess excellent biological importance with
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