Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives

Leifeng Wang; Fengjin Wu; Jiean Chen; David A. Nicewicz; Yong Huang

doi:10.1002/anie.201702940

Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives

Leifeng Wang, Fengjin Wu, Jiean Chen, David A. Nicewicz^*, Yong Huang

^*Corresponding author for this work

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

75 Citations (Scopus)

Abstract

We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.

Original language	English
Pages (from-to)	6896-6900
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	24
DOIs	https://doi.org/10.1002/anie.201702940
Publication status	Published - 6 Jun 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

cycloaddition
organocatalysis
photoredox chemistry
radical reactions
tetralin

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10.1002/anie.201702940

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abstract = "We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.",

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T1 - Visible-Light-Mediated [4+2] Cycloaddition of Styrenes

T2 - Synthesis of Tetralin Derivatives

AU - Wang, Leifeng

AU - Wu, Fengjin

AU - Chen, Jiean

AU - Nicewicz, David A.

AU - Huang, Yong

PY - 2017/6/6

Y1 - 2017/6/6

N2 - We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.

AB - We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.

KW - cycloaddition

KW - organocatalysis

KW - photoredox chemistry

KW - radical reactions

KW - tetralin

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M3 - Journal Article

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SN - 1433-7851

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SP - 6896

EP - 6900

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 24

ER -

Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives

Abstract

Bibliographical note

Keywords

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