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

Devi Prasan Ojha; Kandikere Ramaiah Prabhu

doi:10.1021/ol503114n

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

Devi Prasan Ojha
, Kandikere Ramaiah Prabhu

Research output: Contribution to journal › Article › peer-review

76 Scopus citations

Abstract

A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).

Original language	English
Pages (from-to)	18-21
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	1
DOIs	https://doi.org/10.1021/ol503114n
State	Published - 2 Jan 2015
Externally published	Yes

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

abstract = "A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).",

author = "Ojha, \{Devi Prasan\} and Prabhu, \{Kandikere Ramaiah\}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2015",

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day = "2",

doi = "10.1021/ol503114n",

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T1 - Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes

T2 - A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones

AU - Ojha, Devi Prasan

AU - Prabhu, Kandikere Ramaiah

PY - 2015/1/2

Y1 - 2015/1/2

N2 - A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).

AB - A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).

UR - https://www.scopus.com/pages/publications/84926472888

U2 - 10.1021/ol503114n

DO - 10.1021/ol503114n

M3 - Article

AN - SCOPUS:84926472888

SN - 1523-7060

VL - 17

SP - 18

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JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

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

Abstract

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