14 C—C Bond Formation in Water through Cross-Dehydrogenative Coupling
Book
Editor: Maiti, D.
Title: Cross-Dehydrogenative Coupling
Print ISBN: 9783132455245; Online ISBN: 9783132455269; Book DOI: 10.1055/b000000640
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
Abstract
The development of efficient procedures for useful reactions continues to be of great importance in organic synthesis. In the past decades, cross-dehydrogenative coupling (CDC) has been extensively investigated as one of the most efficient and sustainable synthetic approaches for the construction of C—C (or C—X) bonds. Cross-dehydrogenative coupling can be applied to produce new C—C or C—X bonds (X = N, O, S, P) under oxidative conditions, without prefunctionalization of reactants, by efficient and simple routes. Conventionally, these reactions have generally been performed in dry organic solvents as it is thought that water molecules may react with the reaction intermediates and catalytic species, hindering catalytic processes. However, in recent years, water has been successfully used as an alternative reaction medium for efficient cross-dehydrogenative coupling reactions. The obvious advantages of using water are its abundance, non-flammability, non-toxicity, and environmental friendliness. This review highlights recent progress in the formation of C—C bonds through cross-dehydrogenative coupling in water.
Key words
cross-dehydrogenative coupling - C—C bond formation - water - catalysis - green chemistry- 1 Metal-Catalyzed Cross-Coupling Reactions. de Meijere A, Diederich F. Wiley-VCH; Weinheim, Germany 2004
- 5 Science of Synthesis Cross Coupling and Heck-Type Reactions. Molander GA, Wolfe JP, Larhed M. Thieme; Stuttgart 2013
- 17 Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB. Angew. Chem. Int. Ed. 2005; 44: 3275
- 22 Huang Y, Xin Z, Yao W, Hu Q, Li Z, Xiao L, Yang B, Zhang J. Chem. Commun. (Cambridge) 2018; 54: 13587
- 23 Meng Q.-Y, Liu Q, Zhong J.-J, Zhang H.-H, Li Z.-J, Chen B, Tung C.-H, Wu L.-Z. Org. Lett. 2012; 14: 5992
- 29 Ambala S, Thatikonda T, Sharma S, Munagala G, Yempalla KR, Vishwakarma RA, Singh PP. Org. Biomol. Chem. 2015; 13: 11341
- 32 Surendra Babu GV, Sai Prathima P, Perumgani PC, Sridhar B, Rao TV, Rao MM. Heteroat. Chem. 2018; 29: e21 423
- 45 Qiu Y, Kong W.-J, Struwe J, Sauermann N, Rogge T, Scheremetjew A, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 5828