8-exo-dig-Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic AuI Catalysts

Mamoru Ito; Daisuke Inoue; Asahi Takaki; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1002/ejoc.201801037

8-exo-dig-Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic Au^I Catalysts

Mamoru Ito, Daisuke Inoue, Asahi Takaki, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

6 Citations (Scopus)

Abstract

The cationic Au^I-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the Au^I complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.

Original language	English
Pages (from-to)	4740-4747
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	34
DOIs	https://doi.org/10.1002/ejoc.201801037
Publication status	Published - 2018 Sept 16

Keywords

Carbene ligands
Dibenzodiazocine
Gold
Homogeneous catalysis
Hydroarylation

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201801037

Cite this

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title = "8-exo-dig-Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic AuI Catalysts",

abstract = "The cationic AuI-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.",

keywords = "Carbene ligands, Dibenzodiazocine, Gold, Homogeneous catalysis, Hydroarylation",

author = "Mamoru Ito and Daisuke Inoue and Asahi Takaki and Kanyiva, {Kyalo Stephen} and Takanori Shibata",

note = "Funding Information: This work was supported by a Mitsubishi Materials Corporation and Waseda University Joint Cooperation Grant. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Ito, Mamoru

AU - Inoue, Daisuke

AU - Takaki, Asahi

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by a Mitsubishi Materials Corporation and Waseda University Joint Cooperation Grant. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/9/16

Y1 - 2018/9/16

N2 - The cationic AuI-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.

AB - The cationic AuI-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.

KW - Carbene ligands

KW - Dibenzodiazocine

KW - Gold

KW - Homogeneous catalysis

KW - Hydroarylation

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