1.4. 6 Hydrothiolation, Hydroalkoxylation, and Hydroaryloxylation
Book
Editors: Cazin, C. ; Nolan, S.
Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1
Print ISBN: 9783132012813; Online ISBN: 9783132407633; Book DOI: 10.1055/b-004-132254
1st edition © 2017. 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: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
Hydrothiolation, hydroalkoxylation, and hydroaryloxylation reactions of carbon–carbon triple or double bonds, which belong to the broader family of hydroelementation reactions, conveniently lead to the formation of vinyl sulfides, alkyl sulfides, vinyl ethers, or alkyl ethers. Well-defined complexes of late transition metals with N-heterocyclic carbene ligands can efficiently promote these reactions under milder conditions and with better stereo- and regiocontrol compared to other methods employing free radicals or strong acids/bases.
Key words
hydrothiolation - hydroalkoxylation - hydroaryloxylation - alkenes - alkynes - allenes - ethers - thioethers - sulfides - nickel - rhodium - copper - gold - palladium - N-heterocyclic carbenes- 3 Castarlenas, R, Di Giuseppe, A, Pérez-Torrente, JJ, Oro, LA. Angew. Chem.. 2013; 125: 223 Angew. Chem. Int. Ed.. 2013; 52: 211
- 4 Malyshev, DA, Scott, NM, Marion, N, Stevens, ED, Ananikov, VP, Beletskaya, IP, Nolan, SP. Organometallics. 2006; 25: 4462
- 6 Di Giuseppe, A, Castarlenas, R, Pérez-Torrente, JJ, Crucianelli, M, Polo, V, Sancho, R, Lahoz, FJ, Oro, LA. J. Am. Chem. Soc.. 2012; 134: 8171
- 7 Palacio, L, Artigas, MJ, Polo, V, Lahoz, FJ, Castarlenas, R, Pérez-Torrente, JJ, Oro, LA. ACS Catal.. 2013; 3: 2910
- 9 Delp, SA, Munro-Leighton, C, Goj, LA, Ramírez, MA, Gunnoe, TB, Petersen, JL, Boyle, PD. Inorg. Chem.. 2007; 46: 2365
- 10 Munro-Leighton, C, Delp, SA, Alsop, NM, Blue, ED, Gunnoe, TB. Chem. Commun. (Cambridge). 2008; 111
- 12 Biasiolo, L, Trinchillo, M, Belanzoni, P, Belpassi, L, Busico, V, Ciancaleoni, G, DʼAmora, A, Macchioni, A, Tarantelli, F, Zuccaccia, D. Chem.–Eur. J.. 2014; 20: 14594
- 15 Gómez-Suárez, A, Gasperini, D, Vummaleti, SVC, Poater, A, Cavallo, L, Nolan, SP. ACS Catal.. 2014; 4: 2701
- 20 Pouy, MJ, Delp, SA, Uddin, J, Ramdeen, VM, Cochrane, NA, Fortman, GC, Gunnoe, TB, Cundari, TR, Sabat, M, Myers, WH. ACS Catal.. 2012; 2: 2182
- 26 Oonishi, Y, Gómez-Suárez, A, Martin, AR, Nolan, SP. Angew. Chem.. 2013; 125: 9949 Angew. Chem. Int. Ed.. 2013; 52: 9767