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Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes: A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones

Devi Prasan Ojha and Kandikere Ramaiah Prabhu*

*Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, Karnataka, India, Email: prabhuorgchem.iisc.ernet.in

D. P. Ojha, K. R. Prabhu, Org. Lett., 2015, 17, 18-21.

DOI: 10.1021/ol503114n (free Supporting Information)


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Abstract

Trapping of a diazo species in an intermolecular fashion by two independent ion species in tandem at the carbene center installs an electrophile and a nucleophile on the same carbon. This metal-free concept enables regioselective syntheses of various vinyl halides, vinyl sulfones, and alkyne derivatives.

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Key Words

alkenyl halides, vinyl bromides, vinyl iodides, NBS, NIS


ID: J54-Y2015