Universität zu Köln

Jarvis, Claire L., Richers, Matthew T., Breugst, Martin ORCID: 0000-0003-0950-8858, Houk, K. N. and Seidel, Daniel ORCID: 0000-0001-6725-111X (2014). Redox-Neutral alpha-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals. Org. Lett., 16 (13). S. 3556 - 3560. WASHINGTON: AMER CHEMICAL SOC. ISSN 1523-7052

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Abstract

Secondary amines react with thiosalicylaldehydes in the presence of catalytic amounts of acetic acid to generate ring-fused N,S-acetals in redox-neutral fashion. A broad range of amines undergo alpha-sulfenylation, including challenging substrates such morpholine, thiomorpholine, and piperazines. Computational studies employing density functional theory indicate that acetic acid reduces the energy barriers of two separate steps, both of which involve proton transfer.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Jarvis, Claire L. UNSPECIFIED UNSPECIFIED UNSPECIFIED Richers, Matthew T. UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Houk, K. N. UNSPECIFIED UNSPECIFIED UNSPECIFIED Seidel, Daniel UNSPECIFIED orcid.org/0000-0001-6725-111X UNSPECIFIED
URN:	urn:nbn:de:hbz:38-434036
DOI:	10.1021/ol501509b
Journal or Publication Title:	Org. Lett.
Volume:	16
Number:	13
Page Range:	S. 3556 - 3560
Date:	2014
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 C-H BOND; ACTIVATED ACID AMIDES; AZOMETHINE YLIDES; ORGANIC-SYNTHESIS; AROMATIC THIACYCLOLS; SYNTHETIC ASPECTS; TERMINAL ALKYNES; HYDRIDE TRANSFER; CYCLIC AMINES; FUNCTIONALIZATION Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/43403