Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

Pratheepkumar Annamalai; Huan Chang Hsiao; Selvam Raju; Yi Hsuan Fu; Pei Ling Chen; Jia Cherng Horng; Yi Hung Liu; Shih-Ching Chuang

doi:10.1021/acs.orglett.9b00119

Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

Pratheepkumar Annamalai, Huan Chang Hsiao, Selvam Raju, Yi Hsuan Fu, Pei Ling Chen, Jia Cherng Horng, Yi Hung Liu, Shih-Ching Chuang^*

^*此作品的通信作者

應用化學系

研究成果: Article › 同行評審

13 引文斯高帕斯（Scopus）

摘要

A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.

原文	English
頁（從 - 到）	1182-1186
頁數	5
期刊	Organic Letters
卷	21
發行號	4
DOIs	https://doi.org/10.1021/acs.orglett.9b00119
出版狀態	Published - 15 2月 2019

存取文件

10.1021/acs.orglett.9b00119

其它文件與鏈接

Link to publication in Scopus

引用此

@article{d7cc1865a6d9470aa428060b78f7112c,

title = "Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates",

abstract = "A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.",

author = "Pratheepkumar Annamalai and Hsiao, {Huan Chang} and Selvam Raju and Fu, {Yi Hsuan} and Chen, {Pei Ling} and Horng, {Jia Cherng} and Liu, {Yi Hung} and Shih-Ching Chuang",

year = "2019",

month = feb,

day = "15",

doi = "10.1021/acs.orglett.9b00119",

language = "English",

volume = "21",

pages = "1182--1186",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

AU - Annamalai, Pratheepkumar

AU - Hsiao, Huan Chang

AU - Raju, Selvam

AU - Fu, Yi Hsuan

AU - Chen, Pei Ling

AU - Horng, Jia Cherng

AU - Liu, Yi Hung

AU - Chuang, Shih-Ching

PY - 2019/2/15

Y1 - 2019/2/15

N2 - A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.

AB - A palladium-catalyzed C-H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C-H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C-H bond functionalizations. Additionally, nondirected C-H bond functionalization at the C-4′ position with alkenes rendered complete C-H functionalization of five C-H bonds that formed a stable hexasubstituted benzene ring.

UR - http://www.scopus.com/inward/record.url?scp=85061274815&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b00119

DO - 10.1021/acs.orglett.9b00119

M3 - Article

C2 - 30714383

AN - SCOPUS:85061274815

SN - 1523-7060

VL - 21

SP - 1182

EP - 1186

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

摘要

存取文件

其它文件與鏈接

指紋

引用此