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Literature DB >> 30897253

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones.

Micol Santi¹, Darren M C Ould¹, Jan Wenz¹, Yashar Soltani¹, Rebecca L Melen¹, Thomas Wirth¹.

Abstract

A novel metal-free synthesis of 3,3-disubstituted benzofuran-2-(3H)-ones through reacting α-aryl-α-diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α-arylations of α-diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3-disubstituted benzofuranones in good yields.

Entities: Chemical

Keywords: benzofuranone; boron; diazo compounds; metal-free conditions; rearrangement

Year: 2019 PMID： 30897253 DOI： 10.1002/anie.201902985

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

7 in total

1. Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Authors: Hongmei Qin; Qimei Xie; Long He
Journal: RSC Adv Date: 2022-06-06 Impact factor: 4.036

7. Understanding the Influence of Donor-Acceptor Diazo Compounds on the Catalyst Efficiency of B(C₆ F₅ )₃ Towards Carbene Formation.

Authors: Rasool Babaahmadi; Ayan Dasgupta; Christopher J T Hyland; Brian F Yates; Rebecca L Melen; Alireza Ariafard
Journal: Chemistry Date: 2022-01-27 Impact factor: 5.020

7 in total

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones.

1. Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Review 2. Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors.

3. Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines.

4. Reactions of Frustrated Lewis Pairs with Chloro-Diazirines: Cleavage of N=N Double Bonds.

5. Single Electron Transfer to Diazomethane-Borane Adducts Prompts C-H Bond Activations.

6. Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.

7. Understanding the Influence of Donor-Acceptor Diazo Compounds on the Catalyst Efficiency of B(C₆ F₅ )₃ Towards Carbene Formation.

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones.

1. Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Review 2. Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors.

3. Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines.

4. Reactions of Frustrated Lewis Pairs with Chloro-Diazirines: Cleavage of N=N Double Bonds.

5. Single Electron Transfer to Diazomethane-Borane Adducts Prompts C-H Bond Activations.

6. Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.

7. Understanding the Influence of Donor-Acceptor Diazo Compounds on the Catalyst Efficiency of B(C6 F5 )3 Towards Carbene Formation.

7. Understanding the Influence of Donor-Acceptor Diazo Compounds on the Catalyst Efficiency of B(C₆ F₅ )₃ Towards Carbene Formation.