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[2 + 2 + 2]-Cycloaddition Reactions Using Immobilized Alkynes. A Proof of Concept for an Integral Use of the Outcoming Products in Solid-Phase Synthetic Methodologies
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-06-29 00:00:00 , DOI: 10.1021/acs.joc.8b01378
Martín J. Riveira 1 , Cintia M. Diez 1 , Mirta P. Mischne 1 , Ernesto G. Mata 1
Affiliation  

The transition-metal-catalyzed [2 + 2 + 2]-cycloaddition of alkynes has become a powerful atom-economical strategy for aromatic ring construction. Unfortunately, the control of the stereo-, regio-, and chemoselectivity of these processes is usually challenging, and these reactions can potentially lead to complex unuseful mixtures. While solid-phase chemistry has proven to be a successful tool for decreasing the number of cycloadducts formed and for facilitating the purification step, an integral use of the outcoming products in this complex reaction is described herein. By using an immobilized monoalkyne, the transition-metal-catalyzed [2 + 2 + 2]-cycloaddition with soluble 1,6-diyne-esters led to the simultaneous preparation of soluble and solid-supported phthalides, showing a new way to benefit from solid-phase synthetic methodologies.

中文翻译:

使用固定的炔烃的[2 + 2 + 2]-环加成反应。固相合成方法中即将使用的产物的整体使用的概念验证

炔烃的过渡金属催化[2 + 2 + 2]-环加成反应已成为强有力的芳香环结构的原子经济策略。不幸的是,对这些过程的立体,区域和化学选择性的控制通常具有挑战性,并且这些反应可能潜在地导致复杂的无用的混合物。尽管固相化学已被证明是减少形成的环加合物的数量并促进纯化步骤的成功工具,但本文描述了在此复杂反应中整体使用即将得到的产物。通过使用固定的单炔烃,过渡金属催化的[2 + 2 + 2]-环与可溶性1,6-二炔-酯的加成反应导致同时制备可溶性和固体负载的邻苯二甲酸酯,显示了一种新的受益途径固相合成方法论。
更新日期:2018-06-29
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