Silver-Mediated Radical C(sp3)-H Biphosphinylation and Nitration of β-Alkynyl Ketones for Accessing Functional Isochromenes

Jun Sun; Jiang Kai Qiu; Ya Nan Wu; Wen Juan Hao; Cheng Guo; Guigen Li; Shu Jiang Tu; Bo Jiang

doi:10.1021/acs.orglett.6b03546

Silver-Mediated Radical C(sp³)-H Biphosphinylation and Nitration of β-Alkynyl Ketones for Accessing Functional Isochromenes

Jun Sun, Jiang Kai Qiu, Ya Nan Wu, Wen Juan Hao, Cheng Guo, Guigen Li, Shu Jiang Tu, Bo Jiang

Chemistry and Biochemistry

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

69 Scopus citations

Abstract

Silver-mediated C(sp³)-H functionalization and 6-endo-dig oxo-cyclization of conjugated β-alkynyl ketones have been established under oxidative conditions. The reaction leads to the concise formation of a wide range of isochromenes via C(sp³)-H bond-breaking and radical addition steps. Dual and monofunctional isochromene products were selectively controlled by using either electron-rich or electron-deficient radical sources.

Original language	English
Pages (from-to)	754-757
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.6b03546
State	Published - Feb 17 2017

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abstract = "Silver-mediated C(sp3)-H functionalization and 6-endo-dig oxo-cyclization of conjugated β-alkynyl ketones have been established under oxidative conditions. The reaction leads to the concise formation of a wide range of isochromenes via C(sp3)-H bond-breaking and radical addition steps. Dual and monofunctional isochromene products were selectively controlled by using either electron-rich or electron-deficient radical sources.",

author = "Jun Sun and Qiu, {Jiang Kai} and Wu, {Ya Nan} and Hao, {Wen Juan} and Cheng Guo and Guigen Li and Tu, {Shu Jiang} and Bo Jiang",

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doi = "10.1021/acs.orglett.6b03546",

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T1 - Silver-Mediated Radical C(sp3)-H Biphosphinylation and Nitration of β-Alkynyl Ketones for Accessing Functional Isochromenes

AU - Sun, Jun

AU - Qiu, Jiang Kai

AU - Wu, Ya Nan

AU - Hao, Wen Juan

AU - Guo, Cheng

AU - Li, Guigen

AU - Tu, Shu Jiang

AU - Jiang, Bo

PY - 2017/2/17

Y1 - 2017/2/17

N2 - Silver-mediated C(sp3)-H functionalization and 6-endo-dig oxo-cyclization of conjugated β-alkynyl ketones have been established under oxidative conditions. The reaction leads to the concise formation of a wide range of isochromenes via C(sp3)-H bond-breaking and radical addition steps. Dual and monofunctional isochromene products were selectively controlled by using either electron-rich or electron-deficient radical sources.

AB - Silver-mediated C(sp3)-H functionalization and 6-endo-dig oxo-cyclization of conjugated β-alkynyl ketones have been established under oxidative conditions. The reaction leads to the concise formation of a wide range of isochromenes via C(sp3)-H bond-breaking and radical addition steps. Dual and monofunctional isochromene products were selectively controlled by using either electron-rich or electron-deficient radical sources.

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U2 - 10.1021/acs.orglett.6b03546

DO - 10.1021/acs.orglett.6b03546

M3 - Article

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AN - SCOPUS:85013420707

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JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Silver-Mediated Radical C(sp³)-H Biphosphinylation and Nitration of β-Alkynyl Ketones for Accessing Functional Isochromenes

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