Development and Scale-up of an Efficient Miyaura Borylation Process Using Tetrahydroxydiboron

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• 作者：Sing R. Gurung ; Christopher Mitchell ; Jie Huang ; Marco Jonas ; Josiah D. Strawser ; Elena Daia ; Andrew Hardy ; Erin O’Brien ; Frederick Hicks ; Charles D. Papageorgiou
• 刊名：Organic Process Research & Development
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：21
• 期：1
• 页码：65-74
• 全文大小：507K
• ISSN：1520-586X

文摘

A revised Miyaura borylation process has been developed using tetrahydroxydiboron that avoids the use of bis(pinacolato) diboron and hence the need to hydrolyze the resulting boronic ester to its corresponding acid. The process was greatly simplified and successfully scaled-up in the pilot plant on a 65 kg scale, reducing plant cycle time and resulting in a 47% overall cost reduction. Furthermore, methodology for the study of the oxygen sensitivity of the process is reported that allowed for optimization of the amount of tetrahydroxydiboron and catalyst used. These studies also demonstrated an oxygen-induced decomposition of tetrahydroxydiboron.