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Literature DB >> 23521626

Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes.

Marcos G Suero¹, Elliott D Bayle, Beatrice S L Collins, Matthew J Gaunt.

Abstract

Copper catalysts enable the electrophilic carbofunctionalization of alkynes with vinyl- and diaryliodonium triflates. The new process forms highly substituted alkenyl triflates from a range of alkynes via a pathway that is opposite to classical carbometalation. The alkenyl triflate products can be elaborated through cross-coupling reactions to generate synthetically useful tetrasubstituted alkenes.

Entities: Chemical

Mesh：

Substances：
Alkenes
Alkynes
Copper

Year: 2013 PMID： 23521626 DOI： 10.1021/ja401840j

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

Keyword Cloud
Cited

20 in total

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

Authors: Beryl X Li; Diane N Le; Kyle A Mack; Andrew McClory; Ngiap-Kie Lim; Theresa Cravillion; Scott Savage; Chong Han; David B Collum; Haiming Zhang; Francis Gosselin
Journal: J Am Chem Soc Date: 2017-07-26 Impact factor: 15.419

2. Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors: Jason M Stevens; David W C MacMillan
Journal: J Am Chem Soc Date: 2013-08-05 Impact factor: 15.419

3. Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

Authors: Harshkumar H Patel; Matthew S Sigman
Journal: J Am Chem Soc Date: 2016-10-25 Impact factor: 15.419

4. Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Authors: Nicolas Gigant; François Quintin; Jan-E Bäckvall
Journal: J Org Chem Date: 2015-02-16 Impact factor: 4.354

5. Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

Authors: Elise Cahard; Henry P J Male; Matthieu Tissot; Matthew J Gaunt
Journal: J Am Chem Soc Date: 2015-06-19 Impact factor: 15.419

10. Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines.

Authors: Rodolphe Beaud; Robert J Phipps; Matthew J Gaunt
Journal: J Am Chem Soc Date: 2016-09-30 Impact factor: 15.419

Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes.

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

2. Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

3. Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

4. Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

5. Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

6. Zinc(II) catalyzed conversion of alkynes to vinyl triflates in the presence of silyl triflates.

7. syn-1,2-carboboration of alkynes with borenium cations.

8. A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis.

9. Dual visible light photoredox and gold-catalyzed arylative ring expansion.

10. Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines.