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Literature DB >> 17295542

A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents.

Alberto Spaggiari¹, Daniele Vaccari, Paolo Davoli, Giovanni Torre, Fabio Prati.

Abstract

A new application of (PhO)3P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.

Entities: Chemical

Year: 2007 PMID： 17295542 DOI： 10.1021/jo061346g

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

16 in total

1. Low Pressure Vinylation of Aryl and Vinyl Halides via Heck-Mizoroki Reactions Using Ethylene.

Authors: Craig R Smith; T V Rajanbabu
Journal: Tetrahedron Date: 2010-01-30 Impact factor: 2.457

2. Formation of vinyl-, vinylhalide- or acyl-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed enantioselective conjugate additions of Si-containing vinylaluminums to β-substituted cyclic enones.

Authors: Tricia L May; Jennifer A Dabrowski; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2010-12-20 Impact factor: 15.419

3. Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

Authors: Julie L Hofstra; Kelsey E Poremba; Alex M Shimozono; Sarah E Reisman
Journal: Angew Chem Int Ed Engl Date: 2019-09-19 Impact factor: 15.336

4. Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

Authors: Fang Gao; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2010-08-18 Impact factor: 15.419

10. Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.

Authors: Tsung-Hao Fu; William T McElroy; Mariam Shamszad; Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents.

1. Low Pressure Vinylation of Aryl and Vinyl Halides via Heck-Mizoroki Reactions Using Ethylene.

2. Formation of vinyl-, vinylhalide- or acyl-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed enantioselective conjugate additions of Si-containing vinylaluminums to β-substituted cyclic enones.

3. Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

4. Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

5. Chemical and biological studies of nakiterpiosin and nakiterpiosinone.

6. Synthesis and structure revision of nakiterpiosin.

7. Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course.

8. Formal syntheses of naturally occurring welwitindolinones.

9. HBr-DMPU: The First Aprotic Organic Solution of Hydrogen Bromide.

10. Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.