2.2 C—C Bond Formation by Alkyl C—H Activation
Book
Editor: Yu, J.-Q.
Title: Catalytic Transformations via C-H Activation 2
Print ISBN: 9783132057210; Online ISBN: 9783132404137; Book DOI: 10.1055/b-004-129675
1st edition © 2015 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Type: Multivolume Edition
Abstract
In comparison to the wealth of methods recently developed for the catalytic functionalization of the C(sp2)—H bonds of arenes and hetarenes, relatively little work has focused on the functionalization of the unactivated C(sp3)—H bonds of alkyl fragments. This chapter highlights selected examples of the fast-growing literature on the catalytic functionalization of unactivated C(sp3)—H bonds through organometallic C—H activation, with an emphasis on the most synthetically useful methods. It covers heteroatom-directed C(sp3)—H activation with regard to cross coupling with alkenes, alkynes, and carbon monoxide, organoboron reagents, diaryliodonium salts, and organic halides. Also included is C(sp3)—H activation/intramolecular C—C coupling induced by oxidative addition and nondirected intermolecular C(sp3)—H arylation.
Key words
C(sp3)—H bond activation - carbon—carbon coupling - transition metals - palladium catalysis - ruthenium catalysis - alkylation- 15 Chatani N, Asaumi T, Ikeda T, Yorimitsu S, Ishii Y, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2000; 122: 12882
- 16 Chatani N, Asaumi T, Yorimitsu S, Ikeda T, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2001; 123: 10935
- 17 Bergman SD, Storr TE, Prokopcová H, Aelvoet K, Diels G, Meerpoel L, Maes BUW. Chem.–Eur. J. 2012; 18: 10393
- 24 Prokopcová H, Bergman SD, Aelvoet K, Smout V, Herrebout W, Van der Veken B, Meerpoel L, Maes BUW. Chem.–Eur. J. 2010; 16: 13063
- 28 Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
- 59 Chaumontet M, Piccardi R, Audic N, Hitce J, Peglion J.-L, Clot E, Baudoin O. J. Am. Chem. Soc. 2008; 130: 15157
- 60 Rousseaux S, Davi M, Sofack-Kreutzer J, Pierre C, Kefalidis CE, Clot E, Fagnou K, Baudoin O. J. Am. Chem. Soc. 2010; 132: 10706
- 72 Sofack-Kreutzer J, Martin N, Renaudat A, Jazzar R, Baudoin O. Angew. Chem. Int. Ed. 2012; 51: 10399
- 82 Martin N, Pierre C, Davi M, Jazzar R, Baudoin O. Chem.–Eur. J. 2012; 18: 4480 Chem.–Eur. J. 2014; 20: 12341