Catalytic Dibenzocyclooctene Synthesis via Cobalt(III)–Carbene Radical and ortho‐Quinodimethane Intermediates

The metalloradical activation of ortho‐benzallylaryl N‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single‐electron reactivity of the redox non‐innocent carbene intermediate. This method offers a novel route to prepare eight‐me...

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Vydané v:	Angewandte Chemie International Edition Ročník 57; číslo 1; s. 140 - 145
Hlavní autori:	te Grotenhuis, Colet, van den Heuvel, Naudin, van der Vlugt, Jarl Ivar, de Bruin, Bas
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	WEINHEIM Wiley 02.01.2018 Wiley Subscription Services, Inc John Wiley and Sons Inc
Vydanie:	International ed. in English
Predmet:	Base metal carbene radicals Catalysis Chemical synthesis Chemistry Chemistry, Multidisciplinary Cobalt Communication Communications dibenzocyclooctenes Hydrazones Intermediates metalloradicals ortho-quinodimethanes Physical Sciences Reaction mechanisms Science & Technology carbene radicals REAGENTS VERSATILE ortho-quinodimethanes 8-MEMBERED RINGS CONSTRUCTION dibenzocyclooctenes metalloradicals CYCLOPROPANATION cobalt CYCLIZATION N-TOSYLHYDRAZONES
ISSN:	1433-7851, 1521-3773, 1521-3773
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Abstract	The metalloradical activation of ortho‐benzallylaryl N‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single‐electron reactivity of the redox non‐innocent carbene intermediate. This method offers a novel route to prepare eight‐membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene−Caryl cyclization. The desired eight‐membered‐ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII–carbene radical intermediates followed by dissociation of an ortho‐quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical‐type intermediates was confirmed by trapping experiments. Metalloradical activation of the shown N‐tosyl hydrazones with [Co(TPP)] provides an effective method for the construction of a series of unique dibenzocyclooctenes in good to excellent yields. The proposed reaction mechanism involves intramolecular hydrogen atom transfer to the key CoIII–carbene radical followed by dissociation of an ortho‐quinodimethane, which then undergoes 8π cyclization.
AbstractList	The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single-electron reactivity of the redox non-innocent carbene intermediate. This method offers a novel route to prepare eight-membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene -Caryl cyclization. The desired eight-membered-ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII -carbene radical intermediates followed by dissociation of an ortho-quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical-type intermediates was confirmed by trapping experiments.The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single-electron reactivity of the redox non-innocent carbene intermediate. This method offers a novel route to prepare eight-membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene -Caryl cyclization. The desired eight-membered-ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII -carbene radical intermediates followed by dissociation of an ortho-quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical-type intermediates was confirmed by trapping experiments. The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single-electron reactivity of the redox non-innocent carbene intermediate. This method offers a novel route to prepare eight-membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective C -C cyclization. The desired eight-membered-ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to Co -carbene radical intermediates followed by dissociation of an ortho-quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical-type intermediates was confirmed by trapping experiments. The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single-electron reactivity of the redox non-innocent carbene intermediate. This method offers a novel route to prepare eight-membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene-Caryl cyclization. The desired eight-membered-ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII-carbene radical intermediates followed by dissociation of an ortho-quinodimethane that undergoes 8πcyclization. The mechanism is supported by DFT calculations, and the presence of radical-type intermediates was confirmed by trapping experiments. The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single-electron reactivity of the redox non-innocent carbene intermediate. This method offers a novel route to prepare eight-membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective C-carbene-C-aryl cyclization. The desired eight-membered-ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to Co-III-carbene radical intermediates followed by dissociation of an ortho-quinodimethane that undergoes 8 pi cyclization. The mechanism is supported by DFT calculations, and the presence of radical-type intermediates was confirmed by trapping experiments. The metalloradical activation of ortho‐benzallylaryl N‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single‐electron reactivity of the redox non‐innocent carbene intermediate. This method offers a novel route to prepare eight‐membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene−Caryl cyclization. The desired eight‐membered‐ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII–carbene radical intermediates followed by dissociation of an ortho‐quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical‐type intermediates was confirmed by trapping experiments. The metalloradical activation of ortho ‐benzallylaryl N ‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single‐electron reactivity of the redox non‐innocent carbene intermediate. This method offers a novel route to prepare eight‐membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective C carbene −C aryl cyclization. The desired eight‐membered‐ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to Co III –carbene radical intermediates followed by dissociation of an ortho ‐quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical‐type intermediates was confirmed by trapping experiments. The metalloradical activation of ortho‐benzallylaryl N‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single‐electron reactivity of the redox non‐innocent carbene intermediate. This method offers a novel route to prepare eight‐membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene−Caryl cyclization. The desired eight‐membered‐ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII–carbene radical intermediates followed by dissociation of an ortho‐quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical‐type intermediates was confirmed by trapping experiments. Metalloradical activation of the shown N‐tosyl hydrazones with [Co(TPP)] provides an effective method for the construction of a series of unique dibenzocyclooctenes in good to excellent yields. The proposed reaction mechanism involves intramolecular hydrogen atom transfer to the key CoIII–carbene radical followed by dissociation of an ortho‐quinodimethane, which then undergoes 8π cyclization.
Author	van der Vlugt, Jarl Ivar van den Heuvel, Naudin te Grotenhuis, Colet de Bruin, Bas
AuthorAffiliation	1 Homogeneous, Supramolecular and Bio-Inspired Catalysis (HomKat) group Van't Hoff Institute for Molecular Sciences (HIMS) University of Amsterdam Science Park 904 1098 XH Amsterdam The Netherlands
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Author_xml	– sequence: 1 givenname: Colet surname: te Grotenhuis fullname: te Grotenhuis, Colet organization: Univ Amsterdam, Vant Hoff Inst Mol Sci HIMS, Homogeneous Supramol & Bioinspired Catalysis HomK, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands – sequence: 2 givenname: Naudin surname: van den Heuvel fullname: van den Heuvel, Naudin organization: Univ Amsterdam, Vant Hoff Inst Mol Sci HIMS, Homogeneous Supramol & Bioinspired Catalysis HomK, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands – sequence: 3 givenname: Jarl Ivar surname: van der Vlugt fullname: van der Vlugt, Jarl Ivar organization: Univ Amsterdam, Vant Hoff Inst Mol Sci HIMS, Homogeneous Supramol & Bioinspired Catalysis HomK, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands – sequence: 4 givenname: Bas orcidid: 0000-0002-3482-7669 surname: de Bruin fullname: de Bruin, Bas email: B.deBruin@uva.nl organization: Univ Amsterdam, Vant Hoff Inst Mol Sci HIMS, Homogeneous Supramol & Bioinspired Catalysis HomK, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/29155465$$D View this record in MEDLINE/PubMed
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Keywords	carbene radicals REAGENTS VERSATILE ortho-quinodimethanes 8-MEMBERED RINGS CONSTRUCTION dibenzocyclooctenes metalloradicals CYCLOPROPANATION cobalt CYCLIZATION N-TOSYLHYDRAZONES
Language	English
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Snippet	The metalloradical activation of ortho‐benzallylaryl N‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled... The metalloradical activation of ortho ‐benzallylaryl N ‐tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled... The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled...
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SubjectTerms	Base metal carbene radicals Catalysis Chemical synthesis Chemistry Chemistry, Multidisciplinary Cobalt Communication Communications dibenzocyclooctenes Hydrazones Intermediates metalloradicals ortho-quinodimethanes Physical Sciences Reaction mechanisms Science & Technology
Title	Catalytic Dibenzocyclooctene Synthesis via Cobalt(III)–Carbene Radical and ortho‐Quinodimethane Intermediates
URI	https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201711028 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000418798600009 https://www.ncbi.nlm.nih.gov/pubmed/29155465 https://www.proquest.com/docview/1980706720 https://www.proquest.com/docview/1966446922 https://pubmed.ncbi.nlm.nih.gov/PMC5767734
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