Universität zu Köln

Breugst, Martin ORCID: 0000-0003-0950-8858 and Reissig, Hans-Ulrich ORCID: 0000-0002-1912-9635 (2020). The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition. Angew. Chem.-Int. Edit., 59 (30). S. 12293 - 12308. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

Full text not available from this repository.

Abstract

The concept of 1,3-dipolar cycloadditions was presented by Rolf Huisgen 60 years ago. Previously unknown reactive intermediates, for example azomethine ylides, were introduced to organic chemistry and the (3+2) cycloadditions of 1,3-dipoles to multiple-bond systems (Huisgen reaction) developed into one of the most versatile synthetic methods in heterocyclic chemistry. In this Review, we present the history of this research area, highlight important older reports, and describe the evolution and further development of the concept. The most important mechanistic and synthetic results are discussed. Quantum-mechanical calculations support the concerted mechanism always favored by R. Huisgen; however, in extreme cases intermediates may be involved. The impact of 1,3-dipolar cycloadditions on the click chemistry concept of K. B. Sharpless will also be discussed.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Reissig, Hans-Ulrich UNSPECIFIED orcid.org/0000-0002-1912-9635 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-333008
DOI:	10.1002/anie.202003115
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	59
Number:	30
Page Range:	S. 12293 - 12308
Date:	2020
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
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 HINDERED THIOCARBONYL YLIDES; CLICK CHEMISTRY; DIAZO-COMPOUNDS; 1.3-DIPOLARE CYCLOADDITIONEN; FULMINIC ACID; DIRADICAL MECHANISM; BENZONITRILE OXIDE; AZOMETHINE YLIDES; ORGANIC-CHEMISTRY; CYCLO-ADDITIONS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/33300