Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates

Ravindra S. Phatake; Venkannababu Mullapudi; Vivek C. Wakchaure; Chepuri V. Ramana

doi:10.1021/acs.orglett.6b03573

Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates

Ravindra S. Phatake, Venkannababu Mullapudi, Vivek C. Wakchaure, Chepuri V. Ramana

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

26 Scopus citations

Abstract

The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).

Original language	English
Pages (from-to)	372-375
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.6b03573
State	Published - 20 Jan 2017
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates",

abstract = "The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).",

author = "Phatake, {Ravindra S.} and Venkannababu Mullapudi and Wakchaure, {Vivek C.} and Ramana, {Chepuri V.}",

note = "Funding Information: We thank the CSIR for funding this project under the 12 FYP ORIGIN Program (CSC0108) and a research fellowship to RSP. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.orglett.6b03573",

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AU - Phatake, Ravindra S.

AU - Mullapudi, Venkannababu

AU - Wakchaure, Vivek C.

AU - Ramana, Chepuri V.

PY - 2017/1/20

Y1 - 2017/1/20

N2 - The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).

AB - The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).

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EP - 375

JO - Organic Letters

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IS - 2

ER -

Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates

Abstract

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