BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines: Route to C2-alkenylated benzoxazoles and benzimidazoles

Xian Rong Song; Yi Feng Qiu; Bo Song; Xin Hua Hao; Ya Ping Han; Pin Gao; Xue Yuan Liu; Yong Min Liang

doi:10.1021/jo502761x

BF₃·Et₂O-promoted cleavage of the C_sp-C_sp2 bond of 2-propynolphenols/anilines: Route to C2-alkenylated benzoxazoles and benzimidazoles

Xian Rong Song
, Yi Feng Qiu
, Bo Song
, Xin Hua Hao
, Ya Ping Han
, Pin Gao
, Xue Yuan Liu
, Yong Min Liang

Lanzhou University

科研成果: 期刊稿件 › 文章 › 同行评审

26 引用（Scopus）

摘要

A novel BF₃·Et₂O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a C_sp-C_sp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.

源语言	英语
页（从-至）	2263-2271
页数	9
期刊	Journal of Organic Chemistry
卷	80
期	4
DOI	https://doi.org/10.1021/jo502761x
出版状态	已出版 - 20 2月 2015
已对外发布	是

访问文件

10.1021/jo502761x

其它文件与链接

链接到 Scopus 的出版物

引用此

@article{5948fcdd34164e48b039221dd9dfaa42,

title = "BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines: Route to C2-alkenylated benzoxazoles and benzimidazoles",

abstract = "A novel BF3·Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a Csp-Csp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.",

author = "Song, \{Xian Rong\} and Qiu, \{Yi Feng\} and Bo Song and Hao, \{Xin Hua\} and Han, \{Ya Ping\} and Pin Gao and Liu, \{Xue Yuan\} and Liang, \{Yong Min\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = feb,

day = "20",

doi = "10.1021/jo502761x",

language = "英语",

volume = "80",

pages = "2263--2271",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines

T2 - Route to C2-alkenylated benzoxazoles and benzimidazoles

AU - Song, Xian Rong

AU - Qiu, Yi Feng

AU - Song, Bo

AU - Hao, Xin Hua

AU - Han, Ya Ping

AU - Gao, Pin

AU - Liu, Xue Yuan

AU - Liang, Yong Min

PY - 2015/2/20

Y1 - 2015/2/20

N2 - A novel BF3·Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a Csp-Csp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.

AB - A novel BF3·Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a Csp-Csp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.

UR - https://www.scopus.com/pages/publications/84923338566

U2 - 10.1021/jo502761x

DO - 10.1021/jo502761x

M3 - 文章

C2 - 25611545

AN - SCOPUS:84923338566

SN - 0022-3263

VL - 80

SP - 2263

EP - 2271

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines: Route to C2-alkenylated benzoxazoles and benzimidazoles

摘要

访问文件

其它文件与链接

学术指纹

引用此

BF₃·Et₂O-promoted cleavage of the C_sp-C_sp2 bond of 2-propynolphenols/anilines: Route to C2-alkenylated benzoxazoles and benzimidazoles