Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)-C(sp3) Cross-Coupling via Radical Sorting
Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationallyconvenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readilyundergo radical activation, and the resulting open-shel...
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| Vydáno v: | Journal of the American Chemical Society Ročník 144; číslo 14; s. 6185 - 6192 |
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| Hlavní autoři: | , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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WASHINGTON
Amer Chemical Soc
13.04.2022
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| ISSN: | 0002-7863, 1520-5126, 1520-5126 |
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| Abstract | Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationallyconvenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readilyundergo radical activation, and the resulting open-shell intermediates can subsequently participate in transition metal catalysis. Inthis report, we describe the C(sp3)-C(sp3) cross-coupling of alcohols and carboxylic acids through the dual combination ofN-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highlycongested quaternary carbon centers from the corresponding tertiary alcohols or tertiary carboxylic acids. We demonstrate thesynthetic applications of this methodology to alcoholC1-alkylation and formal homologation, as well as to the late-stagefunctionalization of drugs, natural products, and biomolecules. |
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| AbstractList | Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationally convenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readily undergo radical activation, and the resulting open-shell intermediates can subsequently participate in transition metal catalysis. In this report, we describe the C(
)-C(
) cross-coupling of alcohols and carboxylic acids through the dual combination of
-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highly congested quaternary carbon centers from the corresponding tertiary alcohols or tertiary carboxylic acids. We demonstrate the synthetic applications of this methodology to alcohol
-alkylation and formal homologation, as well as to the late-stage functionalization of drugs, natural products, and biomolecules. Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationally convenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readily undergo radical activation, and the resulting open-shell intermediates can subsequently participate in transition metal catalysis. In this report, we describe the C(sp3)-C(sp3) cross-coupling of alcohols and carboxylic acids through the dual combination of N-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highly congested quaternary carbon centers from the corresponding tertiary alcohols or tertiary carboxylic acids. We demonstrate the synthetic applications of this methodology to alcohol C1-alkylation and formal homologation, as well as to the late-stage functionalization of drugs, natural products, and biomolecules.Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationally convenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readily undergo radical activation, and the resulting open-shell intermediates can subsequently participate in transition metal catalysis. In this report, we describe the C(sp3)-C(sp3) cross-coupling of alcohols and carboxylic acids through the dual combination of N-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highly congested quaternary carbon centers from the corresponding tertiary alcohols or tertiary carboxylic acids. We demonstrate the synthetic applications of this methodology to alcohol C1-alkylation and formal homologation, as well as to the late-stage functionalization of drugs, natural products, and biomolecules. Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationallyconvenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readilyundergo radical activation, and the resulting open-shell intermediates can subsequently participate in transition metal catalysis. Inthis report, we describe the C(sp3)-C(sp3) cross-coupling of alcohols and carboxylic acids through the dual combination ofN-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highlycongested quaternary carbon centers from the corresponding tertiary alcohols or tertiary carboxylic acids. We demonstrate thesynthetic applications of this methodology to alcoholC1-alkylation and formal homologation, as well as to the late-stagefunctionalization of drugs, natural products, and biomolecules. |
| Author | MacMillan, David W. C. Sakai, Holt A. |
| Author_xml | – sequence: 1 givenname: Holt A. orcidid: 0000-0002-9338-1484 surname: Sakai fullname: Sakai, Holt A. organization: Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA – sequence: 2 givenname: David W. C. orcidid: 0000-0001-6447-0587 surname: MacMillan fullname: MacMillan, David W. C. email: dmacmill@princeton.edu organization: Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35353531$$D View this record in MEDLINE/PubMed |
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| Keywords | HYDROGEN PHOTOREDOX STRATEGY DEOXYGENATION ARYLATION DISCOVERY ALKYL-HALIDES |
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| Snippet | Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationallyconvenient functional groups in organic... Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationally convenient functional groups in organic... |
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| SubjectTerms | Alcohols Alkylation Carbon - chemistry Carboxylic Acids - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)-C(sp3) Cross-Coupling via Radical Sorting |
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