A Universal Organocatalyst for Selective Mono-, Di-, and Triboration of Terminal Alkynes,ACS Catalysis

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A Universal Organocatalyst for Selective Mono-, Di-, and Triboration of Terminal Alkynes
ACS Catalysis ( IF 11.3 ) Pub Date : 2023-06-01 , DOI: 10.1021/acscatal.3c01435
Son H. Doan ₁ , Binh Khanh Mai ₂ , Thanh Vinh Nguyen ₁

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Multiboronate compounds are valuable synthetic building blocks for the construction of complex organic architectures via cross-coupling chemistry at the C–B bonds. Hence, there has been a tremendous amount of work in the past decades to develop practical multiboration reactions. Many of the developed methods start from alkynes, the most versatile synthetic precursors for multiboronates, and use transition-metal complexes as catalysts. However, several drawbacks such as low efficiency, poor selectivity, and narrow substrate and catalyst scopes remain major challenges to be addressed in this research area. Herein, we report the development of a universal organocatalytic system to promote the mono-, di-, and triboration of terminal alkynes in a highly efficient and selective manner. The reaction outcomes can be manipulated at will by varying the catalyst loading, reagent stoichiometry, and reaction time. A combined computational and experimental mechanistic study offers interesting insights into the selectivity of these sequential reactions.

中文翻译：

用于末端炔烃选择性单硼化、双硼化和三硼化的通用有机催化剂

多硼酸盐化合物是有价值的合成构件，可通过 C-B 键的交叉偶联化学构建复杂的有机结构。因此，在过去的几十年中，已经进行了大量的工作来开发实用的多硼化反应。许多已开发的方法都是从炔烃（最通用的多硼酸盐合成前体）开始，并使用过渡金属络合物作为催化剂。然而，效率低、选择性差、底物和催化剂范围窄等几个缺点仍然是该研究领域需要解决的主要挑战。在此，我们报告了一种通用有机催化系统的开发，以高效和选择性的方式促进末端炔烃的单硼化、二硼化和三硼化。可以通过改变催化剂负载量、试剂化学计量和反应时间来随意控制反应结果。结合计算和实验的机理研究为这些连续反应的选择性提供了有趣的见解。

更新日期：2023-06-01

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