Chandrashekar Hediyala B, Maji Arun, Halder Ganga, Banerjee Sucheta, Bhattacharyya Sayan, Maiti Debabrata
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India.
Chem Commun (Camb). 2019 May 28;55(44):6201-6204. doi: 10.1039/c9cc01737b.
The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.
在水存在的情况下,通过桑德迈尔型反应合成芳基硼酸酯仍然是一项重大挑战。在此,我们报道了使用水溶性MPA包覆的量子点(QD)光催化剂在水存在的情况下对重氮盐进行硼化反应。温和酸性条件下的双相体系对于防止分解和竞争性二硫键形成至关重要。本方法提供了更广泛的底物和硼化剂范围。此外,该催化体系具有显著高的周转数(TON)。本方法能够有效区分硼酸和硼酸酯之间细微的反应活性差异。机理研究表明存在激发态电子转移途径。