修饰胆汁酸的合成——钯催化的C(sp)-H（杂）芳基化反应

Synthesis of modified bile acids palladium-catalyzed C(sp)-H (hetero)arylation.

作者信息

Borade Somnath Arjun, Naharwal Sushma, Bhambri Himanshi, Mandal Sanjay K, Bajaj Kiran, Chitkara Deepak, Sakhuja Rajeev

机构信息

Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India.

Department of Chemical Sciences, Indian Institute of Science Education and Research Mohali, Sector 81, SAS Nagar, Manuali P. O., Mohali, Punjab 140306, India.

出版信息

Org Biomol Chem. 2023 Aug 23;21(33):6719-6729. doi: 10.1039/d3ob00916e.

DOI:10.1039/d3ob00916e

PMID:37555287

Abstract

A Pd(II)-catalyzed strategy for the diastereo- and regioselective (hetero)arylation of unactivated C(sp)-H bonds in bile acids is accomplished with aryl and heteroaryl iodides under solvent-free conditions using the 8-aminoquinoline auxiliary as a directing group. This methodology demonstrated excellent functional group tolerance with respect to aryl/heteroaryl iodides on -protected -(quinolin-8-yl)cholyl/deoxycholyl amides to afford β-C(sp)-H (hetero)arylated products in good-to-excellent yields. Moreover, the 8-aminoquinoline (AQ) auxiliary can easily be removed to obtain modified bile acids.

摘要

一种用于胆汁酸中未活化C(sp)-H键的非对映和区域选择性（杂）芳基化的钯（II）催化策略，是在无溶剂条件下，以8-氨基喹啉辅助基团作为导向基团，与芳基和杂芳基碘化物实现的。该方法对于-保护的-（喹啉-8-基）胆酰基/脱氧胆酰基酰胺上的芳基/杂芳基碘化物表现出优异的官能团耐受性，以良好至优异的产率得到β-C(sp)-H（杂）芳基化产物。此外，8-氨基喹啉（AQ）辅助基团可以很容易地除去以获得修饰的胆汁酸。