Pyridinium Salt Forming Rh(III)-Catalyzed Annulation Reaction of Secondary Allylamines with Internal Alkynes and Its Application to Surface Modification of a Mesoporous Material

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

doi:10.1021/acs.orglett.7b03654

Pyridinium Salt Forming Rh(III)-Catalyzed Annulation Reaction of Secondary Allylamines with Internal Alkynes and Its Application to Surface Modification of a Mesoporous Material

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

Department of Chemistry

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

11 Citations (Scopus)

Abstract

A Rh(III)-catalyzed C-H activation reaction has been developed for the preparation of pyridinium salts from secondary allylamines and internal alkynes. The pyridinium salts formed by this N-annulation reaction have interesting fluorescence properties. This protocol has been applied to the surface modification of mesoporous silica materials to generate functionalized silica that can be used for the detection of nitrobenzene.

Original language	English
Pages (from-to)	264-267
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03654
Publication status	Published - 2018 Jan 5

Bibliographical note

Funding Information:
†Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Republic of Korea ‡New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Republic of Korea

Funding Information:
This study was supported by the grant from LG Chem. (Grant 2015-11-0067) and the National Research Foundation of Korea (NRF) (Grant 2017-R-1-A2b4009460).

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.7b03654

Cite this

@article{a0e6342b3d2940d59555cf4a2a18a52c,

title = "Pyridinium Salt Forming Rh(III)-Catalyzed Annulation Reaction of Secondary Allylamines with Internal Alkynes and Its Application to Surface Modification of a Mesoporous Material",

abstract = "A Rh(III)-catalyzed C-H activation reaction has been developed for the preparation of pyridinium salts from secondary allylamines and internal alkynes. The pyridinium salts formed by this N-annulation reaction have interesting fluorescence properties. This protocol has been applied to the surface modification of mesoporous silica materials to generate functionalized silica that can be used for the detection of nitrobenzene.",

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

note = "Funding Information: †Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Republic of Korea ‡New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Republic of Korea Funding Information: This study was supported by the grant from LG Chem. (Grant 2015-11-0067) and the National Research Foundation of Korea (NRF) (Grant 2017-R-1-A2b4009460). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2018",

month = jan,

day = "5",

doi = "10.1021/acs.orglett.7b03654",

language = "English",

volume = "20",

pages = "264--267",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Pyridinium Salt Forming Rh(III)-Catalyzed Annulation Reaction of Secondary Allylamines with Internal Alkynes and Its Application to Surface Modification of a Mesoporous Material

AU - Han, Ye Ri

AU - Shim, Su Hyang

AU - Kim, Dong Su

AU - Jun, Chul Ho

N1 - Funding Information: †Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Republic of Korea ‡New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Republic of Korea Funding Information: This study was supported by the grant from LG Chem. (Grant 2015-11-0067) and the National Research Foundation of Korea (NRF) (Grant 2017-R-1-A2b4009460). Publisher Copyright: © 2017 American Chemical Society.

PY - 2018/1/5

Y1 - 2018/1/5

N2 - A Rh(III)-catalyzed C-H activation reaction has been developed for the preparation of pyridinium salts from secondary allylamines and internal alkynes. The pyridinium salts formed by this N-annulation reaction have interesting fluorescence properties. This protocol has been applied to the surface modification of mesoporous silica materials to generate functionalized silica that can be used for the detection of nitrobenzene.

AB - A Rh(III)-catalyzed C-H activation reaction has been developed for the preparation of pyridinium salts from secondary allylamines and internal alkynes. The pyridinium salts formed by this N-annulation reaction have interesting fluorescence properties. This protocol has been applied to the surface modification of mesoporous silica materials to generate functionalized silica that can be used for the detection of nitrobenzene.

UR - http://www.scopus.com/inward/record.url?scp=85040235282&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85040235282&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b03654

DO - 10.1021/acs.orglett.7b03654

M3 - Article

C2 - 29244517

AN - SCOPUS:85040235282

SN - 1523-7060

VL - 20

SP - 264

EP - 267

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Pyridinium Salt Forming Rh(III)-Catalyzed Annulation Reaction of Secondary Allylamines with Internal Alkynes and Its Application to Surface Modification of a Mesoporous Material

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this