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Literature DB >> 22142167

Directing group-controlled hydrosilylation: regioselective functionalization of alkyne.

Yuuya Kawasaki¹, Youhei Ishikawa, Kazunobu Igawa, Katsuhiko Tomooka.

Abstract

Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopropargylic alcohol derivatives. DMVS also has an accelerating effect that allows group-selective hydrosilylation of the DMVS-attached alkyne prior to that of other alkynes. Combined hydrosilylation and transformation reactions of the resulting silylalkenes afford various tri-substituted alkenes and multi-oxy-functionalized compounds with high regioselectivity from unsymmetric alkynes.

Entities: Chemical

Year: 2011 PMID： 22142167 DOI： 10.1021/ja209553f

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

1. Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

Authors: Zachary D Miller; Wei Li; Tomás R Belderrain; John Montgomery
Journal: J Am Chem Soc Date: 2013-10-03 Impact factor: 15.419

2. Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides.

Authors: Keri A Steiniger; Tristan H Lambert
Journal: Org Lett Date: 2021-10-06 Impact factor: 6.072

3. Interplay between the Directing Group and Multifunctional Acetate Ligand in Pd-Catalyzed anti-Acetoxylation of Unsymmetrical Dialkyl-Substituted Alkynes.

Authors: Javier Corpas; Enrique M Arpa; Romain Lapierre; Inés Corral; Pablo Mauleón; Ramón Gómez Arrayás; Juan C Carretero
Journal: ACS Catal Date: 2022-05-19 Impact factor: 13.700

Directing group-controlled hydrosilylation: regioselective functionalization of alkyne.

1. Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

2. Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides.

3. Interplay between the Directing Group and Multifunctional Acetate Ligand in Pd-Catalyzed anti-Acetoxylation of Unsymmetrical Dialkyl-Substituted Alkynes.

4. Regioselective allene hydroarylation via one-pot allene hydrosilylation/Pd-catalyzed cross-coupling.

5. Nickel(0)-catalyzed linear-selective hydroarylation of unactivated alkenes and styrenes with aryl boronic acids.

6. Regiocontrol in the cobalt-catalyzed hydrosilylation of alkynes.

7. Hydroxy group-enabled highly regio- and stereo-selective hydrocarboxylation of alkynes.

8. Regio-selective and stereo-selective hydrosilylation of internal alkynes catalyzed by ruthenium complexes.