Transition-metal-free access to benzyl ethers <i>via</i> aerobic cross-dehydrogenative coupling of benzylic C(sp<sup>3</sup>)–H bonds with alcohols

Zhang, Xiao; Li, Wenjie; Yu, Yang; Luo, Min; Bai, Hua; Shi, Lei; Li, Hao

doi:10.1039/d3gc04070d

Green Chem.

2024

DOI: 10.1039/d3gc04070d

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Transition-metal-free access to benzyl ethers via aerobic cross-dehydrogenative coupling of benzylic C(sp³)–H bonds with alcohols

Xiao Zhang,

Wenjie Li,

Yang Yu

et al.

Abstract: We have developeda practical KOtBu or KOH-catalyzed aerobic cross-dehydrogenative coupling of benzylic C(sp3)–H with various alcohols utilizing molecular oxygen as the sole oxidant. This transition-metal-free and chemical-oxidant-free methodology could enable...

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Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Bone,

Puleo,

Delost

et al. 2024

Angewandte Chemie

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We disclose a benzylic C–H oxidative coupling reaction with alcohols that proceeds through a synergistic deprotonation, halogenation and substitution sequence. The combination of tert‐butoxide bases with 2‐halothiophene halogen oxidants enables the first general protocol for generating and using benzyl halides through a deprotonative pathway. In contrast to existing radical‐based pathways for C–H functionalization, this process is guided by C–H acidity trends. This gives rise to new synthetic capabilities, including the ability to functionalize diverse methyl(hetero)arenes, tolerance of oxidizable and nucleophilic functional groups, precision site‐selectivity for polyalkylarenes and use of a double C–H etherification process to controllably oxidize methylarenes to benzaldehydes.

show abstract

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Bone,

Puleo,

Delost

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Bone,

Puleo,

Delost

et al. 2024

Angew Chem Int Ed

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show abstract

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Transition-metal-free access to benzyl ethers via aerobic cross-dehydrogenative coupling of benzylic C(sp³)–H bonds with alcohols

Abstract: We have developeda practical KOtBu or KOH-catalyzed aerobic cross-dehydrogenative coupling of benzylic C(sp3)–H with various alcohols utilizing molecular oxygen as the sole oxidant. This transition-metal-free and chemical-oxidant-free methodology could enable...

Cited by 2 publications

References 76 publications

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

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Transition-metal-free access to benzyl ethers via aerobic cross-dehydrogenative coupling of benzylic C(sp3)–H bonds with alcohols

Abstract: We have developeda practical KOtBu or KOH-catalyzed aerobic cross-dehydrogenative coupling of benzylic C(sp3)–H with various alcohols utilizing molecular oxygen as the sole oxidant. This transition-metal-free and chemical-oxidant-free methodology could enable...

Cited by 2 publications

References 76 publications

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

Direct Benzylic C−H Etherification Enabled by Base‐Promoted Halogen Transfer

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Product

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Transition-metal-free access to benzyl ethers via aerobic cross-dehydrogenative coupling of benzylic C(sp³)–H bonds with alcohols