Catalysis Based on C−I⋅⋅⋅π Halogen Bonds: Electrophilic Activation of 2-Alkenylindoles by Cationic Halogen-Bond Donors for [4+2] Cycloadditions

Satoru Kuwano; Takumi Suzuki; Masahiro Yamanaka; Ryosuke Tsutsumi; Takayoshi Arai

doi:10.1002/anie.201904689

Catalysis Based on C−I⋅⋅⋅π Halogen Bonds: Electrophilic Activation of 2-Alkenylindoles by Cationic Halogen-Bond Donors for [4+2] Cycloadditions

Satoru Kuwano, Takumi Suzuki, Masahiro Yamanaka, Ryosuke Tsutsumi, Takayoshi Arai

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

34 Citations (Scopus)

Abstract

Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles, catalyzed by cationic halogen-bond donors, were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C−I⋅⋅⋅π halogen bonds.

Original language	English
Pages (from-to)	10220-10224
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	30
DOIs	https://doi.org/10.1002/anie.201904689
Publication status	Published - 2019 Jul 22
Externally published	Yes

Keywords

cycloaddition
density-functional calculations
halogen bonding
heterocycles
noncovalent bonds

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201904689

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Catalysis Based on C−I⋅⋅⋅π Halogen Bonds : Electrophilic Activation of 2-Alkenylindoles by Cationic Halogen-Bond Donors for [4+2] Cycloadditions. / Kuwano, Satoru; Suzuki, Takumi; Yamanaka, Masahiro et al.

In: Angewandte Chemie - International Edition, Vol. 58, No. 30, 22.07.2019, p. 10220-10224.

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

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abstract = "Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles, catalyzed by cationic halogen-bond donors, were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C−I⋅⋅⋅π halogen bonds.",

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author = "Satoru Kuwano and Takumi Suzuki and Masahiro Yamanaka and Ryosuke Tsutsumi and Takayoshi Arai",

note = "Funding Information: This research is supported by JSPS KAKENHI Grant Number JP19H02709 in Grant-in-Aid for Scientific Research (B), JP16H01004 and JP18H04237 in Precisely Designed Catalysts with Customized Scaffolding, JP18H04660 (Hybrid Catalysis), 19K15553 in Grant-in-Aid for Young Scientists, and the Futaba Research Grant Program of the Futaba Foundation. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/anie.201904689",

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AU - Kuwano, Satoru

AU - Suzuki, Takumi

AU - Yamanaka, Masahiro

AU - Tsutsumi, Ryosuke

AU - Arai, Takayoshi

N1 - Funding Information: This research is supported by JSPS KAKENHI Grant Number JP19H02709 in Grant-in-Aid for Scientific Research (B), JP16H01004 and JP18H04237 in Precisely Designed Catalysts with Customized Scaffolding, JP18H04660 (Hybrid Catalysis), 19K15553 in Grant-in-Aid for Young Scientists, and the Futaba Research Grant Program of the Futaba Foundation. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/7/22

Y1 - 2019/7/22

N2 - Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles, catalyzed by cationic halogen-bond donors, were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C−I⋅⋅⋅π halogen bonds.

AB - Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles, catalyzed by cationic halogen-bond donors, were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C−I⋅⋅⋅π halogen bonds.

KW - cycloaddition

KW - density-functional calculations

KW - halogen bonding

KW - heterocycles

KW - noncovalent bonds

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Catalysis Based on C−I⋅⋅⋅π Halogen Bonds: Electrophilic Activation of 2-Alkenylindoles by Cationic Halogen-Bond Donors for [4+2] Cycloadditions

Abstract

Keywords

ASJC Scopus subject areas

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