Universität zu Köln

Shao, Wen, Lux, Marcel, Breugst, Martin ORCID: 0000-0003-0950-8858 and Klussmann, Martin ORCID: 0000-0002-9026-205X (2019). Radical addition of ketones and cyanide to olefins via acid catalyzed formation of intermediate alkenyl peroxides. Org. Chem. Front., 6 (11). S. 1796 - 1801. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 2052-4129

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Abstract

A Bronsted acid catalyzed method was developed for the synthesis of.-cyanoketones from sulfonyl cyanides, olefins and ketones. The reaction is believed to proceed via intermediate formation of alkenyl peroxides by condensation of ketones with tert-butylhydroperoxide. These unstable compounds decompose by homolytic O-O bond cleavage, generating ketone-derived radicals which add to the olefins and generate the final products after reaction with the sulfonyl cyanide, thereby forming two new C-C bonds. A range of different ketones and olefins can be used, including steroidal ketones and simple alkyl olefins. The products can be further transformed to substituted lactones and piperidines, including a tetracyclic one. This reaction can thus be utilized to gain access to complex molecules from simple starting materials in only a few synthetic steps.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Shao, Wen UNSPECIFIED UNSPECIFIED UNSPECIFIED Lux, Marcel UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Klussmann, Martin UNSPECIFIED orcid.org/0000-0002-9026-205X UNSPECIFIED
URN:	urn:nbn:de:hbz:38-138047
DOI:	10.1039/c9qo00447e
Journal or Publication Title:	Org. Chem. Front.
Volume:	6
Number:	11
Page Range:	S. 1796 - 1801
Date:	2019
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	2052-4129
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 UNACTIVATED ALKENES; CONJUGATE ADDITION; SULFONYL CYANIDES; MICHAEL ADDITIONS; NITRILES; CYANATION; CYANOTRIFLUOROMETHYLATION; REARRANGEMENT; CONSTRUCTION; ABSTRACTION Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/13804