Alshammari Muteb H, Alhunayhin Sultanah M N, Hughes David L, Chambrier Isabelle, Cammidge Andrew N
School of Chemistry, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, U.K.
Org Lett. 2024 Mar 1;26(8):1561-1565. doi: 10.1021/acs.orglett.3c04215. Epub 2024 Feb 19.
-disubstituted porphyrins are highly valuable intermediates across diverse fields, but they pose a significant synthesis challenge in some cases due to scrambling and formation of complex mixtures. Conditions that minimize scrambling also lower yields, but steric hindrance around the meso-aryl substituent can effectively suppress scrambling altogether. Here we report a straightforward approach to valuable trans-AB porphyrin intermediates that are otherwise very difficult to obtain, through use of removable blocking bromide substituents.
二取代卟啉是跨多个领域非常有价值的中间体，但在某些情况下，由于重排和形成复杂混合物，它们带来了重大的合成挑战。使重排最小化的条件也会降低产率，但中位芳基取代基周围的空间位阻可以有效地完全抑制重排。在这里，我们报告了一种直接的方法，通过使用可去除的阻断溴取代基来获得否则很难得到的有价值的反式AB卟啉中间体。
