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Updated: Jul 19, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Synthesis of modified bile acids via palladium-catalyzed C(sp3)-H (hetero)arylation
Somnath Arjun Borade1, Sushma Naharwal1, Himanshi Bhambri2
1Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India. sakhuja.rajeev@gmail.com.
Abstract:
A Pd(II)-catalyzed strategy for the diastereo- and regioselective (hetero)arylation of unactivated C(sp3)-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 O-protected N-(quinolin-8-yl)cholyl/deoxycholyl amides to afford β-C(sp3)-H (hetero)arylated products in good-to-excellent yields. Moreover, the 8-aminoquinoline (AQ) auxiliary can easily be removed to obtain modified bile acids.
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