Sun Huaxing, Wang Jing, Du Zihang, Zhang Kun, Hu Jiefeng, Jing Su
School of Chemistry and Molecular Engineering, Nanjing Tech University, Puzhu Roads 30, Nanjing 211816, China.
State Key Laboratory of Organic Electronics and Information Displays, College of Chemistry and Life Sciences, Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing 210023, China.
Org Lett. 2024 Mar 1;26(8):1618-1622. doi: 10.1021/acs.orglett.4c00001. Epub 2024 Feb 17.
The direct transformation of alkylboron has emerged as a versatile and powerful methodology for creating carbon-carbon and carbon-heteroatom bonds. However, its potential application in the formation of carbon and phosphorus remains unexplored. In this study, we present an alkoxide base-promoted reaction system that enables deborylative phosphination of benzylic organoboronates and geminal bis(boronates) via selective C-B bond cleavage. This approach allows for the synthesis of valuable tertiary phosphines in good yields under mild conditions. The practicality and industrial potential of this approach are underscored by the operational simplicity, broad substrate scope, and easy scalability.
烷基硼的直接转化已成为构建碳-碳和碳-杂原子键的一种通用且强大的方法。然而，其在碳磷键形成方面的潜在应用仍未得到探索。在本研究中，我们提出了一种醇盐碱促进的反应体系，该体系能够通过选择性碳-硼键裂解实现苄基有机硼酸酯和偕二硼酸酯的脱硼膦化反应。这种方法能够在温和条件下以良好的产率合成有价值的叔膦。该方法操作简便、底物范围广且易于扩大规模，突出了其实用性和工业潜力。
