Affiliation:
1. Institute of Pharmaceutical Science and Technology
2. Zhejiang University of Technology
3. Fudan University
Abstract
Abstract
Despite the remarkable advances in the research field of asymmetric catalytic oxidation reactions via hypervalent iodines with simple procedures, high level of efficiency and stereoselectivity over the past few decades, the development of their highly scalable, environmentally benign, and sustainable protocols under the greener organocatalysis paradigm for further industrial translations remains a long-standing synthetic organic chemistry and process engineering challenge. Herein, we design and synthesize a new library of conformationally flexible and recyclable aryl iodine catalysts by utilization of (i) industrial waste (chloramphenicol base) as the scaffold and (ii) inexpensive amino acid residue (threonine) as the chiral source. Our chiral aryl iodine(III) catalysts bearing H-bond donors and a tunable chiral pocket have been successfully applied in diverse robust asymmetric oxidative transformations, e.g., dearomatization, spirolactonization, direct C(sp2)−H/C(sp3)−H cross-coupling, and fluoridation. Our processes feature a column-isolation-free approach, easy-handling operation, and upscaling synthesis, with the catalysts being facilely recycled in particular via precipitation.
Publisher
Research Square Platform LLC
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