Synthesis of Benzoquinolizinium Salts by Rh(III)-Catalyzed Cascade Double N-Annulation Reactions of Allylamines, Diarylacetylenes, and HBF4

Ye Ri Han; Su Hyang Shim; Dong Su Kim; Chul Ho Jun

doi:10.1021/acs.orglett.7b01175

Synthesis of Benzoquinolizinium Salts by Rh(III)-Catalyzed Cascade Double N-Annulation Reactions of Allylamines, Diarylacetylenes, and HBF₄

Ye Ri Han, Su Hyang Shim, Dong Su Kim, Chul Ho Jun

Department of Chemistry

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

30 Citations (Scopus)

Abstract

A new cascade double N-annulation method has been developed for the synthesis of benzoquinolizinium salts. The process takes place between allylamines, internal alkynes, and HBF₄ in the presence of Rh(III)/Cu(II) complexes and leads to formation of multisubstituted benzoquinolizinium salts. Importantly, the resulting benzoquinolizinium salts serve as fluorescent materials whose emission wavelengths can be tuned by selection of appropriate substituents.

Original language	English
Pages (from-to)	2941-2944
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.7b01175
Publication status	Published - 2017 Jun 2

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b01175

Cite this

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abstract = "A new cascade double N-annulation method has been developed for the synthesis of benzoquinolizinium salts. The process takes place between allylamines, internal alkynes, and HBF4 in the presence of Rh(III)/Cu(II) complexes and leads to formation of multisubstituted benzoquinolizinium salts. Importantly, the resulting benzoquinolizinium salts serve as fluorescent materials whose emission wavelengths can be tuned by selection of appropriate substituents.",

author = "Han, {Ye Ri} and Shim, {Su Hyang} and Kim, {Dong Su} and Jun, {Chul Ho}",

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T1 - Synthesis of Benzoquinolizinium Salts by Rh(III)-Catalyzed Cascade Double N-Annulation Reactions of Allylamines, Diarylacetylenes, and HBF4

AU - Han, Ye Ri

AU - Shim, Su Hyang

AU - Kim, Dong Su

AU - Jun, Chul Ho

PY - 2017/6/2

Y1 - 2017/6/2

N2 - A new cascade double N-annulation method has been developed for the synthesis of benzoquinolizinium salts. The process takes place between allylamines, internal alkynes, and HBF4 in the presence of Rh(III)/Cu(II) complexes and leads to formation of multisubstituted benzoquinolizinium salts. Importantly, the resulting benzoquinolizinium salts serve as fluorescent materials whose emission wavelengths can be tuned by selection of appropriate substituents.

AB - A new cascade double N-annulation method has been developed for the synthesis of benzoquinolizinium salts. The process takes place between allylamines, internal alkynes, and HBF4 in the presence of Rh(III)/Cu(II) complexes and leads to formation of multisubstituted benzoquinolizinium salts. Importantly, the resulting benzoquinolizinium salts serve as fluorescent materials whose emission wavelengths can be tuned by selection of appropriate substituents.

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