Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp)-H bonds driven by visible light

Asymmetric cross-dehydrogenative coupling (CDC) of C(sp 3 )-H bonds shows great potential for rapid and stereoselective construction of C-C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reacti...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 14; pp. 4597 - 463
Main Authors Zhou, Kexu, Yu, Ying, Lin, Yu-Mei, Li, Yanjun, Gong, Lei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 20.07.2020
Royal Society of Chemistry
Subjects
Asymmetry
Carbonyl compounds
Carbonyls
Catalysts
chemical bonding
Chemistry
Chemistry, Multidisciplinary
Copper
Coupling (molecular)
Covalent bonds
Dehydrogenation
Enantiomers
enantioselectivity
Green & Sustainable Science & Technology
Green chemistry
light
Oxidants
Oxidizing agents
Oxygen
photocatalysis
Photochemical reactions
Photochemicals
Physical Sciences
Science & Technology
Science & Technology - Other Topics
Stereochemistry
Stereoselectivity
Xanthene
xanthenes
FUNCTIONALIZATION
TRANSITION-METAL CATALYSIS
SP C-H
ETHERS
ACTIVATION
ELECTRON-TRANSFER
MECHANISM
TERTIARY-AMINES
ALKYLATION
ALDEHYDES
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Abstract Asymmetric cross-dehydrogenative coupling (CDC) of C(sp 3 )-H bonds shows great potential for rapid and stereoselective construction of C-C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp 3 )-H precursors. Herein we report our effort towards this goal via copper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C-C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions. An effective and green approach to aerobic cross-dehydrogenative coupling (CDC) reaction between two C(sp 3 )-H precursors has been achieved by copper-based asymmetric photocatalysis.
AbstractList Asymmetric cross-dehydrogenative coupling (CDC) of C(sp 3 )-H bonds shows great potential for rapid and stereoselective construction of C-C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp 3 )-H precursors. Herein we report our effort towards this goal via copper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C-C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions. An effective and green approach to aerobic cross-dehydrogenative coupling (CDC) reaction between two C(sp 3 )-H precursors has been achieved by copper-based asymmetric photocatalysis.
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp³)–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp³)–H precursors. Herein we report our effort towards this goal via copper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C–C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions.
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp 3 )–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp 3 )–H precursors. Herein we report our effort towards this goal via copper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C–C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions.
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp3)–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp3)–H precursors. Herein we report our effort towards this goal via copper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C–C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions.
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp(3))-H bonds shows great potential for rapid and stereoselective construction of C-C bonds and use of molecular oxygen as the oxidant for such transformations is appealing in the context of green synthetic methodologies. However, the poor reactivity of oxygen at the ground state and the challenges in controlling the stereochemistry make it extremely difficult to access highly enantioselective aerobic CDC reactions of C(sp(3))-H precursors. Herein we report our effort towards this goalviacopper-based asymmetric photocatalysis. A chiral-copper catalyst initiates the visible-light-driven oxidative CDC reaction by molecular oxygen, and governs the stereochemistry. In this way, a diastereo- and enantioselective cross-dehydrogenative coupling between carbonyl compounds and xanthene derivatives has been achieved. This work provides an economic and manageable approach to stereoselective C-C bond formation, and demonstrates a potential application of chiral copper catalysts in difficult asymmetric photochemical reactions.
Author Zhou, Kexu
Lin, Yu-Mei
Gong, Lei
Yu, Ying
Li, Yanjun
AuthorAffiliation iChEM
Xiamen University
College of Chemistry and Chemical Engineering
Key Laboratory of Chemical Biology of Fujian Province
AuthorAffiliation_xml – name: College of Chemistry and Chemical Engineering
– name: Key Laboratory of Chemical Biology of Fujian Province
– name: iChEM
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  givenname: Yu-Mei
  surname: Lin
  fullname: Lin, Yu-Mei
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  givenname: Yanjun
  surname: Li
  fullname: Li, Yanjun
– sequence: 5
  givenname: Lei
  surname: Gong
  fullname: Gong, Lei
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Issue 14
Keywords FUNCTIONALIZATION
TRANSITION-METAL CATALYSIS
SP C-H
ETHERS
ACTIVATION
ELECTRON-TRANSFER
MECHANISM
TERTIARY-AMINES
ALKYLATION
ALDEHYDES
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Snippet Asymmetric cross-dehydrogenative coupling (CDC) of C(sp 3 )-H bonds shows great potential for rapid and stereoselective construction of C-C bonds and use of...
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp 3 )–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of...
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp(3))-H bonds shows great potential for rapid and stereoselective construction of C-C bonds and use of...
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp3)–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of...
Asymmetric cross-dehydrogenative coupling (CDC) of C(sp³)–H bonds shows great potential for rapid and stereoselective construction of C–C bonds and use of...
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SubjectTerms Asymmetry
Carbonyl compounds
Carbonyls
Catalysts
chemical bonding
Chemistry
Chemistry, Multidisciplinary
Copper
Coupling (molecular)
Covalent bonds
Dehydrogenation
Enantiomers
enantioselectivity
Green & Sustainable Science & Technology
Green chemistry
light
Oxidants
Oxidizing agents
Oxygen
photocatalysis
Photochemical reactions
Photochemicals
Physical Sciences
Science & Technology
Science & Technology - Other Topics
Stereochemistry
Stereoselectivity
Xanthene
xanthenes
Title Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp)-H bonds driven by visible light
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