Efficient Diels-Alder reaction of 1,2-benzoquinones with arynes and its utility in one-pot reactions

Trinadh Kaicharla; Sachin Suresh Bhojgude; Akkattu T. Biju

doi:10.1021/ol302997q

Efficient Diels-Alder reaction of 1,2-benzoquinones with arynes and its utility in one-pot reactions

Trinadh Kaicharla, Sachin Suresh Bhojgude, Akkattu T. Biju

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

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Abstract

A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.

Original language	English (US)
Pages (from-to)	6238-6241
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol302997q
State	Published - Dec 21 2012
Externally published	Yes

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abstract = "A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.",

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T1 - Efficient Diels-Alder reaction of 1,2-benzoquinones with arynes and its utility in one-pot reactions

AU - Kaicharla, Trinadh

AU - Bhojgude, Sachin Suresh

AU - Biju, Akkattu T.

PY - 2012/12/21

Y1 - 2012/12/21

N2 - A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.

AB - A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.

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ER -

Efficient Diels-Alder reaction of 1,2-benzoquinones with arynes and its utility in one-pot reactions

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