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Literature DB >> 26180918

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System.

Shoji Fujita¹, Masanori Abe¹, Masatoshi Shibuya¹, Yoshihiko Yamamoto¹.

Abstract

A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

Entities: Chemical

Year: 2015 PMID： 26180918 DOI： 10.1021/acs.orglett.5b01797

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.

Authors: Dake Chen; Ilyas A Berhane; Sherry R Chemler
Journal: Org Lett Date: 2020-06-04 Impact factor: 6.005

2. A multifunctional nanozyme-based enhanced system for tert-butyl hydroquinone assay by surface-enhanced Raman scattering.

Authors: Dezhi Yang; Qiulan Li; Qian Zhang; Yijie Wang; Hong Li; Sai Kumar Tammina; Yaling Yang
Journal: Mikrochim Acta Date: 2021-12-15 Impact factor: 5.833

6. Transition metal-free direct dehydrogenative arylation of activated C(sp³)-H bonds: synthetic ambit and DFT reactivity predictions.

Authors: Kaitlyn Lovato; Lirong Guo; Qing-Long Xu; Fengting Liu; Muhammed Yousufuddin; Daniel H Ess; László Kürti; Hongyin Gao
Journal: Chem Sci Date: 2018-08-27 Impact factor: 9.825

6 in total

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System.

1. Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.

2. A multifunctional nanozyme-based enhanced system for tert-butyl hydroquinone assay by surface-enhanced Raman scattering.

3. Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer.

4. α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.

5. Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis.

6. Transition metal-free direct dehydrogenative arylation of activated C(sp³)-H bonds: synthetic ambit and DFT reactivity predictions.

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System.

1. Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.

2. A multifunctional nanozyme-based enhanced system for tert-butyl hydroquinone assay by surface-enhanced Raman scattering.

3. Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer.

4. α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.

5. Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis.

6. Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: synthetic ambit and DFT reactivity predictions.

6. Transition metal-free direct dehydrogenative arylation of activated C(sp³)-H bonds: synthetic ambit and DFT reactivity predictions.