Universität zu Köln

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:	Creators Email ORCID ORCID Put Code Noel-Duchesneau, Ludovik UNSPECIFIED UNSPECIFIED UNSPECIFIED Lagadic, Elodie UNSPECIFIED UNSPECIFIED UNSPECIFIED Morlet-Savary, Fabrice UNSPECIFIED UNSPECIFIED UNSPECIFIED Lohier, Jean-Francois UNSPECIFIED UNSPECIFIED UNSPECIFIED Chataigner, Isabelle UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Lalevee, Jacques UNSPECIFIED UNSPECIFIED UNSPECIFIED Gaumont, Annie-Claude UNSPECIFIED UNSPECIFIED UNSPECIFIED Lakhdar, Sami UNSPECIFIED orcid.org/0000-0002-1168-7472 UNSPECIFIED
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:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language DONOR-ACCEPTOR COMPLEX; C BOND FORMATION; DIARYLIODONIUM SALTS; RADICAL TRIFLUOROMETHYLATION; PHOTOINITIATING SYSTEMS; OXIDATIVE CYCLIZATION; ORGANIC-SYNTHESIS; DIRECT ARYLATION; ISONITRILES; 2-ISOCYANOBIPHENYLS Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/25559