Pd(NHC)(cinnamyl)Cl-catalyzed Suzuki cross-coupling reaction of aryl sulfonates with arylboronic acids
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ORIGINAL ARTICLE
Pd(NHC)(cinnamyl)Cl‑catalyzed Suzuki cross‑coupling reaction of aryl sulfonates with arylboronic acids Qiwei Wang1,2 · Zhen Dai2,3 · Xiangjie Di2,3 · QingFei Huang2 · Yuanhua Wang4 · Jin Zhu2 Received: 21 August 2019 / Accepted: 30 September 2019 © Springer Nature Switzerland AG 2019
Abstract A series of N-heterocyclic carbene (NHC)–palladium catalysts have been synthesized and applied to catalyze the Suzuki coupling reaction efficiently between aryl sulfonates and arylboronic acids with the potassium phosphate heptahydrate as a base. The desired yields are obtained even with less reactive aryl tosylates or aryl mesylates as substrates. This method was applied successfully to the synthesis of the (R)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propan-1-ol which is the key intermediate of sacubitril, a component of the newly approved antihypertensive drug “Entresto.” Graphic abstract
Keywords N-Heterocyclic carbene · Suzuki cross-coupling reaction · Aryl sulfonates · Palladium catalyst Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-10001-4) contains supplementary material, which is available to authorized users. * Qiwei Wang [email protected] * QingFei Huang [email protected] * Yuanhua Wang [email protected] 1
Department of Chemistry, Xihua University, Chengdu 610039, China
2
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
3
Graduate University of Chinese Academy of Sciences, Beijing 100049, China
4
College of Chemistry, Sichuan University, Chengdu 610065, China
Introduction The Suzuki–Miyaura cross-coupling reaction is one of the most effective methods for the C–C bond formation [1–8]. The resulting products such as styrene, diphenyl and polyene hydrocarbon are widely used in the field of pharmaceutical, material and agricultural chemistry [9–12]. Generally, the highly active aryl triflates as electrophilic substrates have been widely used in Suzuki–Miyaura coupling reactions. However, the aryl sulfonates, such as aryl tosylates, phenyl sulfonates and aryl mesylates, are challenging substrates because sulfonates show less reactivity than corresponding aryl halides and triflates [13–16]. There were only few studies reported reactions with sulfonates as the substrates [17–19]. For instance, Monteiro and coworkers reported that NiCl2(PCy3)2 catalyzed the coupling of aryl sulfonates with arylboronic acids in high
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Molecular Diversity
Scheme 1 Synthesis of precatalysts and structure of catalysts
yields [17]. Compared with phosphine ligands, N-heterocyclic carbenes (NHCs) with significantly bulky “fence” skeleton are stronger electron donators and can tune catalytic activity efficiently by modifying the N-substituted groups. Shao and coworkers used palladium catalyst ([NHC–Pd(II)–Im]) with NHCs as ancillary ligands to catalyze Suzuki reactions using aryl sulfonates as substrates, resulting in 96% yield of the desired product [20]. In 2015, [NHC–Pd(II)
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