Noel-Duchesneau, Ludovik, Lagadic, Elodie, Morlet-Savary, Fabrice, Lohier, Jean-Francois, Chataigner, Isabelle, Breugst, Martin ORCID: 0000-0003-0950-8858, Lalevee, Jacques, Gaumont, Annie-Claude and Lakhdar, Sami ORCID: 0000-0002-1168-7472 (2016). Metal-Free Synthesis of 6-Phosphorylated Phenanthridines: Synthetic and Mechanistic Insights. Org. Lett., 18 (22). S. 5900 - 5904. WASHINGTON: AMER CHEMICAL SOC. ISSN 1523-7052

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Abstract

A novel and efficient method for the generation of phosphinoyl radicals from the combination of diphenyliodonium salt (Ph2I+, -OTf) with triethylamine (Et3N) in the presence of secondary phosphine oxides is reported. By employing this practical and simple approach, a large variety of 6-phosphorylated phenanthridines have been synthesized through the addition of phosphinoyl radicals to isonitriles as, radical acceptors. The reaction works smoothly in the absence of any transition metal or photocatalyst. On the basis of electron paramagnetic resonance (EPR) and density functional discussed. theory (DFT) calculations, the mechanism of this reaction is novel and efficient method for the generation of phosphinoyl radicals from the combination of diphenylio-donium salt (Ph2I+,-OTf) with triethylamine (Et3N) in the presence of secondary phosphine oxides is reported. By employing this practical and simple approach, a large variety of 6-phosphorylated phenanthridines have been synthesized through the addition of phosphinoyl radicals to isonitriles as, radical acceptors. The reaction works smoothly in the absence of any transition metal or photocatalyst. On the basis of electron paramagnetic resonance (EPR) and density functional theory (DFT) calculations, the mechanism of this reaction is discussed.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Noel-Duchesneau, LudovikUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Lagadic, ElodieUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Morlet-Savary, FabriceUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Lohier, Jean-FrancoisUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Chataigner, IsabelleUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Breugst, MartinUNSPECIFIEDorcid.org/0000-0003-0950-8858UNSPECIFIED
Lalevee, JacquesUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Gaumont, Annie-ClaudeUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Lakhdar, SamiUNSPECIFIEDorcid.org/0000-0002-1168-7472UNSPECIFIED
URN: urn:nbn:de:hbz:38-255596
DOI: 10.1021/acs.orglett.6b02983
Journal or Publication Title: Org. Lett.
Volume: 18
Number: 22
Page Range: S. 5900 - 5904
Date: 2016
Publisher: AMER CHEMICAL SOC
Place of Publication: WASHINGTON
ISSN: 1523-7052
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
DONOR-ACCEPTOR COMPLEX; C BOND FORMATION; DIARYLIODONIUM SALTS; RADICAL TRIFLUOROMETHYLATION; PHOTOINITIATING SYSTEMS; OXIDATIVE CYCLIZATION; ORGANIC-SYNTHESIS; DIRECT ARYLATION; ISONITRILES; 2-ISOCYANOBIPHENYLSMultiple languages
Chemistry, OrganicMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/25559

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