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Liu, G. : 2023 Science of Synthesis, 2023/1: Knowledge Updates 2023/1 DOI: 10.1055/sos-SD-147-00202
Knowledge Updates 2023/1

47.1.5.6 Synthesis of Functionalized Alkenes by Metal-Catalyzed Coupling of Carbonyls with Alkynes/Allenes

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Book

Editor: Liu, G. 

Authors: Chen, P. ; Cheng, Z.; Gong, L.-Z. ; Ho, C.-Y.; Jiang, R. ; Jie, X. ; Lei, A. ; Lin, Z.; Liu, B.; Liu, G. ; Liu, Q. ; Liu, X.; Lu, Z. ; Raja, D.; Sayed, M. ; Su, W. ; Tang, S. ; Tao, R.; Wang, J. ; Wang, K. ; Wang, P.-S. ; Yang, P.; You, S.-L. ; Zhao, Y.; Zheng, Y.

Title: Knowledge Updates 2023/1

Print ISBN: 9783132455061; Online ISBN: 9783132455085; Book DOI: 10.1055/b000000844

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 Knowledge Updates



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

In this review, different coupling methodologies between carbonyls and alkynes or allenes affording highly functionalized alkenes are summarized. Two main strategies are discussed in detail: In the first one, electrophilic carbonyl species are utilized in metal-catalyzed reductive coupling reactions assisted by various reductants such as boranes, silanes, and hydrogen gas. In the second one, nucleophilic carbonyl species are employed in coupling reactions with electrophilic π-allyl intermediates generated in situ, resulting in a formal α-allylation of carbonyls. Various representative examples serve to demonstrate the high versatility of these two general strategies, including applications in the total synthesis of complex natural products. High regio- and stereocontrol can be achieved with excellent yields for most of the selected examples. Reports of decarboxylative coupling and metal-free coupling are also included.

Key words

alkenes - alkynes - allenes - aldehydes - ketones - transition-metal catalysis - cross coupling - reductive coupling - π-allyl intermediates - enantioselectivity - regioselectivity
 
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