Enantioselective Cobaltaphotoredox-Catalyzed\nC–H\nActivation

The quest for sustainable strategies in molecular synthesis\nhas\nspurred the emergence of photocatalysis as a particularly powerful\ntechnique. In recent years, the application of photocatalysis in this\ncontext has greatly promoted the development of asymmetric catalysis.\nDespite the impressive advances, enantioselective photoinduced strong\narene C–H activations by cobalt catalysis remain unexplored.\nHerein, we report a strategy that merges organic photoredox catalysis\nand enantioselective cobalt-catalyzed C–H activation, enabling\nthe regio- and stereoselective dual functionalization of indoles in\nan enantioselective fashion. Thereby, the assembly of various chiral\nindolo[2,3-<i>c</i>]isoquinolin-5-ones was realized with\nhigh enantioselectivities of up to 99%. The robustness of the cobaltaphotoredox\ncatalysis was demonstrated through enantioselective C–H activation\nand annulations in a continuous flow to provide straightforward access\nto central and axially chiral molecules.

Publication Details

Journal
Figshare
Published
2024-08-15
DOI
https://doi.org/10.1021/jacs.4c08459.s001
Primary Topic
Historical Studies on Reproduction, Gender, Health, and Societal Changes
Type
article
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article

Enantioselective Cobaltaphotoredox-Catalyzed\nC–H\nActivation

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Historical Studies on Reproduction, Gender, Health, and Societal Changes
article

Enantioselective Cobaltaphotoredox-Catalyzed\nC–H\nActivation

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Abstract

The quest for sustainable strategies in molecular synthesis\nhas\nspurred the emergence of photocatalysis as a particularly powerful\ntechnique. In recent years, the application of photocatalysis in this\ncontext has greatly promoted the development of asymmetric catalysis.\nDespite the impressive advances, enantioselective photoinduced strong\narene C–H activations by cobalt catalysis remain unexplored.\nHerein, we report a strategy that merges organic photoredox catalysis\nand enantioselective cobalt-catalyzed C–H activation, enabling\nthe regio- and stereoselective dual functionalization of indoles in\nan enantioselective fashion. Thereby, the assembly of various chiral\nindolo[2,3-<i>c</i>]isoquinolin-5-ones was realized with\nhigh enantioselectivities of up to 99%. The robustness of the cobaltaphotoredox\ncatalysis was demonstrated through enantioselective C–H activation\nand annulations in a continuous flow to provide straightforward access\nto central and axially chiral molecules.

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Historical Studies on Reproduction, Gender, Health, and Societal Changes
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