Mahmoud R. Saleh, , , Mahmoud Afrasi, , , Ajay H. Bansode, , , Poulami Ghosh, , , Dan E. Wise, , and , Marvin Parasram*,
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Photochromic Oxime Directing Groups for Spatially Controlled Pd-Catalyzed C–H Difunctionalization with Tandem Electrophiles
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.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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