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van Leeuwen, P. W. N. M.: 2014 Science of Synthesis, 2013/7: C-1 Building Blocks in Organic Synthesis 1 DOI: 10.1055/sos-SD-212-00221
C-1 Building Blocks in Organic Synthesis 1

1.2.1 Carbonylation of Alkynes

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Book

Editor: van Leeuwen, P. W. N. M.

Authors: Ballini, R.; Belderrain, T. R.; Bronger, R. P. J.; Clarke, M. L.; Claver, C.; de Vries, J. G.; Feng, X. M.; Fleischer, I.; Fuentes, J. A.; Godard, C.; Goldfuss, B.; Iwasawa, N.; Kamer, P. C. J.; Lin, L. L.; Liu, X. H.; Mejía, E.; Monflier, E.; Mortreux, A.; Nicasio, M. C.; Perandones, B. F.; Petrini, M.; Sauthier, M.; Takaya, J.; Tauchert, M. E.; Tilloy, S.; Vogt, D.

Title: C-1 Building Blocks in Organic Synthesis 1

Subtitle: Additions to Alkenes, Alkynes, and Carbonyl Compounds

Print ISBN: 9783131707611; Online ISBN: 9783132064416; Book DOI: 10.1055/b-003-125818

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: C-1 Building Blocks in Organic Synthesis

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

This chapter provides a concise overview of metal-catalyzed additions to alkynes that involve carbon monoxide and a nucleophilic species, such as water, an alcohol, a thiol, or an amine. Alkynes undergo very efficient hydroalkoxyesterifications of the type extensively studied in alkene carbonylation chemistry, but in this case giving unsaturated esters and seemingly by a different mechanism that allows for a wider range of reaction pathways. In this chapter, examples are presented where relatively subtle changes in substrate structure or competing pathways lead to a range of products; nucleophiles can add to alkynes in an intramolecular fashion prior to carbonylation, or external nucleophiles attack an alkyne to initiate a carbonylation. The carbonylation events can also be terminated in several different ways, especially under oxidative conditions. Several representative experimental procedures are given for the main classes of carbonylation covered.

Key words

alkoxyesterification - hydroalkoxycarbonylation - hydroesterification - hydroxycarbonylation - cyclization - asymmetric synthesis - carbon monoxide - alkynes - atom efficiency
 
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