Cascade Reaction of Alkynols and 7-Oxabenzonorbornadienes Involving Transient Hemiketal Group Directed C-H Activation and Synergistic Rh III /Sc III Catalysis

Deng Yuan Li; Liang Liang Jiang; Shuang Chen; Zheng Lu Huang; Li Dang; Xin Yan Wu; Pei Nian Liu

doi:10.1021/acs.orglett.6b02587

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Cascade Reaction of Alkynols and 7-Oxabenzonorbornadienes Involving Transient Hemiketal Group Directed C-H Activation and Synergistic Rh III /Sc III Catalysis

Journal article

Peer reviewed

Cascade Reaction of Alkynols and 7-Oxabenzonorbornadienes Involving Transient Hemiketal Group Directed C-H Activation and Synergistic Rh III /Sc III Catalysis

Deng Yuan Li, Liang Liang Jiang, Shuang Chen, Zheng Lu Huang, Li Dang, Xin Yan Wu and Pei Nian Liu

Organic letters, Vol.18(19), pp.5134-5137

10/07/2016

DOI: https://doi.org/10.1021/acs.orglett.6b02587

PMID: 27647431

Abstract

Toxicological synergy

Catalysts

Cyclization

Catalysis

Chemical Reactions

As the first cascade C–H activation directed by a transient group, reaction of alkynols and 7-oxabenzonorbornadienes has been achieved via synergistic rhodium and scandium catalysis to afford spirocyclic dihydrobenzo[a]fluorenefurans. This transformation proceeds by a transient hemiketal group directed C–H activation, dehydrative naphthylation, and intramolecular Prins-type cyclization. Mechanistic studies and density functional theory calculations indicate that the rate-determining step is C–H bond cleavage and both the transient hemiketal group and synergistic RhIII/ScIII catalysis play key roles.

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Title: Cascade Reaction of Alkynols and 7-Oxabenzonorbornadienes Involving Transient Hemiketal Group Directed C-H Activation and Synergistic Rh III /Sc III Catalysis
Creators: Deng Yuan Li - Shanghai Key Laboratory of Functional Materials Chemistry and Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China
Liang Liang Jiang - Shanghai Key Laboratory of Functional Materials Chemistry and Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China
Shuang Chen - Shanghai Key Laboratory of Functional Materials Chemistry and Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China
Zheng Lu Huang - Shanghai Key Laboratory of Functional Materials Chemistry and Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China
Li Dang - Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China
Xin Yan Wu - Shanghai Key Laboratory of Functional Materials Chemistry and Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China
Pei Nian Liu - Shanghai Key Laboratory of Functional Materials Chemistry and Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China
Publication Details: Organic letters, Vol.18(19), pp.5134-5137
Publisher: United States
Identifiers: 9923972824401921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Cascade Reaction of Alkynols and 7-Oxabenzonorbornadienes Involving Transient Hemiketal Group Directed C-H Activation and Synergistic Rh III /Sc III Catalysis

Abstract

UN Sustainable Development Goals (SDGs)

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