化学
烷基
卤化物
碘化物
组合化学
正在离开组
分子
有机化学
功能群
催化作用
聚合物
作者
Mingming Huang,Jiefeng Hu,Shasha Shi,Alexandra Friedrich,Johannes Krebs,Stephen A. Westcott,Udo Radius,Todd B. Marder
标识
DOI:10.1002/chem.202200480
摘要
Abstract Defunctionalization of readily available feedstocks to provide alkenes for the synthesis of multifunctional molecules represents an extremely useful process in organic synthesis. Herein, we describe a transition metal‐free, simple and efficient strategy to access alkyl 1,2‐bis(boronate esters) via regio‐ and diastereoselective diboration of secondary and tertiary alkyl halides (Br, Cl, I), tosylates, and alcohols. Control experiments demonstrated that the key to this high reactivity and selectivity is the addition of a combination of potassium iodide and N , N ‐dimethylacetamide (DMA). The practicality and industrial potential of this transformation are demonstrated by its operational simplicity, wide functional group tolerance, and the late‐stage modification of complex molecules. From a drug discovery perspective, this synthetic method offers control of the position of diversification and diastereoselectivity in complex ring scaffolds, which would be especially useful in a lead optimization program.
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