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Updated: Jan 15, 2026
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photochromic Oxime Directing Groups for Spatially Controlled Pd-Catalyzed C-H Difunctionalization with Tandem
Mahmoud R Saleh1, Mahmoud Afrasi1, Ajay H Bansode1
1Department of Chemistry, New York University, 24 Waverly Place, third floor, New York, New York 10003, United States.
None:
Herein, we report the employment of oxime ethers as photochromic directing groups for the controlled functionalization of spatially and inherently distinct C-(sp2)-H/C-(sp3)-H bonds. Our approach features a semi-two-pot protocol for Pd-catalyzed C-(sp2)-H oxygenation, photoisomerization, and Pd-catalyzed C-(sp3)-H arylation for the synthesis of difunctionalized oxime derivatives in a highly selective and controlled manner. Notably, we illustrate the rare utilization of hypervalent iodine reagents as tandem electrophiles for C-H difunctionalization. The reverse sequence of functionalization events can be achieved thermally, thereby providing a platform for full directing group-controlled C-H difunctionalization. Overall, this work highlights that photochromic directing groups can provide an avenue for positionally controlled C-H difunctionalization.
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