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Yoshikai, N. : 2023 Science of Synthesis, 2022/5: Base-Metal Catalysis 1 DOI: 10.1055/sos-SD-238-00029
Base-Metal Catalysis 1

1.2 Copper(I) Hydride Catalyzed Transformations

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Book

Editor: Yoshikai, N. 

Authors: Chatani, N. ; Chemler, S. R. ; Chen, P. ; Dai, H.-X. ; Delcaillau, T.; Fujihara, T. ; Huang, J. ; Iwabuchi, Y. ; Kennedy-Ellis, J. J. ; Ko, C.; Koh, M. J. ; Lee, B. C.; Li, Y.; Lin, L.; Liu, G. ; Ma, D. ; Morandi, B. ; Nakao, Y. ; Ouyang, Y. ; Pang, X.; Qing, F.-L. ; Ren, Y. ; Sasano, Y. ; Shang, Y. ; Shou, J.-Y.; Shu, X.-Z. ; Su, W. ; Tobisu, M. ; Wang, C. ; Xiong, T. ; Xu, H.; Yang, F.; Yoshida, T.; Zhu, S. 

Title: Base-Metal Catalysis 1

Print ISBN: 9783132453807; Online ISBN: 9783132453821; Book DOI: 10.1055/b000000441

1st edition © 2023 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

Copper(I) hydride is a binary metal hydride that, due to the relatively low electropositivity of copper, features a rather covalent metal−hydrogen bond. This readily obtained species can either be pre-prepared or generated in situ, and reacts with various unsaturated bonds or polar single bonds to form intermediates with reactive C—Cu bonds, which can be captured by various electrophiles to form new chemical bonds and new stereocenters. In this chapter, some representative examples in this domain are discussed, with the methods divided into four sections based on the different kinds of electrophiles. The first three sections cover asymmetric C—N, C—C, and C—B bond formation with various electrophilic nitrogen sources, carbon-based reagents, and boranes, and the last section focuses on some racemic transformations.

Key words

copper(I) hydride - copper catalysis - alkenes - alkynes - aldehydes - ketones - hydroamination - hydrocarbonation - allylation - hydroboration
 
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