Tandem Azolation/Aromatization of Tetrahydronaphthalenes with Hydrogen Evolution via Organophotoredox/Cobalt Dual Catalysis

Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)­azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, ste...

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Published inOrganic letters Vol. 27; no. 13; pp. 3284 - 3290
Main Authors Huang, Cheng, Tang, Sheng, Wang, Chen-Lu, Kang, Chen, Wang, Ying, Jing, Yaru, Ye, Zhong-Ming, Wei, Zhenhong, Cai, Hu
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.04.2025
Subjects
aromatization
catalytic activity
cobalt
cross-coupling reactions
dehydrogenation
hydrogen production
irradiation
light
redox reactions
tetrahydronaphthalenes
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Abstract Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)­azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C–H/N–H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.
AbstractList Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)­azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C–H/N–H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.
Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of -(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a -centered radical mediated C-H/N-H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.
Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C-H/N-H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C-H/N-H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.
Author Tang, Sheng
Ye, Zhong-Ming
Wei, Zhenhong
Jing, Yaru
Huang, Cheng
Wang, Ying
Kang, Chen
Wang, Chen-Lu
Cai, Hu
AuthorAffiliation School of Materials Science and Engineering, PCFM Lab
School of Chemistry and Chemical Engineering
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Snippet Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for...
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SubjectTerms aromatization
catalytic activity
cobalt
cross-coupling reactions
dehydrogenation
hydrogen production
irradiation
light
redox reactions
tetrahydronaphthalenes
Title Tandem Azolation/Aromatization of Tetrahydronaphthalenes with Hydrogen Evolution via Organophotoredox/Cobalt Dual Catalysis
URI http://dx.doi.org/10.1021/acs.orglett.5c00640
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