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Cazin, C.  et al.: 2018 Science of Synthesis, 2016/5b: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2 DOI: 10.1055/sos-SD-224-00063
N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

2.3 Cyclization Reactions

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Book

Editors: Cazin, C. ; Nolan, S.

Authors: Basle, O.; Broggi, J.; Claver, C.; Clavier, H.; Collins, S. K.; Costabile, C.; Crevisy, C.; Crozet, D.; Davies, A.; Diesendruck, C. E.; Felten, S.; Godard, C.; Grela, K.; Holtz-Mulholland, M.; Jana, A.; Johnson, J.; Lapkin, A.; Liu, J.; Lombardía, A.; Louie, J.; Malecki, P.; Mauduit, M.; Munz, D.; Nelson, D.; Peñafiel, I.; Schmid, T.; Slugovc, C.; Smith, A. D.; Thieuleux, C.; Zhong, Y.

Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 2

Print ISBN: 9783132414006; Online ISBN: 9783132414044; Book DOI: 10.1055/b-004-140260

1st edition © 2018 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

This chapter presents a detailed overview of current research into N-heterocyclic carbene (NHC) coordinated, transition-metal-catalyzed cyclization reactions. Highly efficient and economical access to pharmacologically relevant moieties, such as carbo- and heterocycles, is crucial in synthetic chemistry. Though cyclizations are atom-economical, historically harsh reaction conditions, poor substrate tolerance, and low product selectivity severely limited the practicality of such reactions. However, transition-metal catalysts based on copper, gold, palladium, nickel, rhodium, cobalt, and iron have allowed for the rapid synthesis of cyclization products in good to high yield and with high selectivity. In addition, these cyclizations tolerate starting materials bearing a variety of functional groups. Symmetric and asymmetric NHC ligands have proven to be critical for success in generating efficient transition-metal based catalytic systems. The electronic and steric diversity of NHC ligands allows for the fine-tuning of the transition-metal catalyst, which has resulted in effective [n + m]-cycloaddition reactions, inter- and intramolecular cycloisomerization reactions, and rearrangement reactions.

Key words

cobalt catalysis - copper catalysis - cyclization - cycloaddition - cycloisomerization - gold catalysis - iron catalysis - N-heterocyclic carbenes - nickel catalysis - palladium catalysis - rearrangements - rhodium catalysis - transition-metal catalysis
 
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