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Cazin, C.  et al.: 2017 Science of Synthesis, 2016/5a: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1 DOI: 10.1055/sos-SD-223-00199
N-Heterocyclic Carbenes in Catalytic Organic Synthesis

1.4.6 Hydrothiolation, Hydroalkoxylation, and Hydroaryloxylation

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Buch

Herausgeber: Cazin, C. ; Nolan, S.

Autoren: Albrecht, M.; Baudrenghien, L.; Bielawski, C.; Biffis, A.; Cavallo, L.; Cazin, C. ; César, V.; Chetcuti, M.; Cuenca, A.; de Frémont, P.; Elie, M.; Fairlamb, I.; Falivene, L.; Fernandez Gutierrez, M. E.; Gagné, M. R.; Gaillard, S.; Huynh, H.; Kalck, P.; Kuwano, R.; Lastovickova, D.; Lavigne, G.; Makida, Y.; Marko, I.; Martin, A.; Nahra, F. ; Nakao, Y.; Ogasawara, M. ; Payne, P.; Renaud, J.; Ronson, T.; Ruamps, M.; Segarra Almela, C.; Teator, A.; Trzeciak, A.; Tubaro, C.; Urrutigoity, M.; Vummaleti, S.; Whittlesey, M.; Yuan, D.

Titel: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1

Print ISBN: 9783132012813; Online ISBN: 9783132407633; Buch-DOI: 10.1055/b-004-132254

1st edition © 2017. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

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Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

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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.

Schlüsselwörter

hydrothiolation - hydroalkoxylation - hydroaryloxylation - alkenes - alkynes - allenes - ethers - thioethers - sulfides - nickel - rhodium - copper - gold - palladium - N-heterocyclic carbenes
 
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