Rhodium-Catalysed [4+2] Annulation of Aromatic Oximes with Terminal Alkenes by C-H/N-O Functionalization towards 3,4-Dihydroisoquinolines

被引：13

作者：

Zhang, Xu ^{[1
,2
]}

Ouyang, Xuan-Hui ^{[2
]}

Li, Yang ^{[2
]}

Chen, Bo ^{[1
]}

Li, Jin-Heng ^{[1
,2
,3
]}

机构：

[1] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China

[2] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 21期

基金：

中国国家自然科学基金;

关键词：

alkenes; oximes; rhodium; annulation; dihydroisoquinolines; ISOQUINOLINE ALKALOIDS; H FUNCTIONALIZATION; ACTIVATION; ACCESS; RH; KETONE; DERIVATIVES; ALKYNES; ROUTE;

D O I：

10.1002/adsc.201900922

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Rhodium (Rh)-catalysed [4+2] annulation of aromatic oximes with common terminal alkenes for the synthesis of 3,4-dihydroisoquinolines is presented. Through the cooperation of a Rh(III) catalyst and a catalytic amount of K2HPO4 base, the reaction enables the formation of two new bonds, a C(sp(2))-C(sp(3)) bond and a C(sp(3))-N bond, in a single reaction via functionalization of both the C-H and N-O bonds and provides a practical method to produce 3,4-dihydroisoquinolines with exquisite selectivity and excellent compatibility of functional groups.

引用

页码：4955 / 4960

页数：6

共 27 条

[1] Merging rhodium-catalysed C-H activation and hydroamination in a highly selective [4+2] imine/alkyne annulation
Manan, Rajith S.
Zhao, Pinjing
NATURE COMMUNICATIONS, 2016, 7
[2] Merging rhodium-catalysed C–H activation and hydroamination in a highly selective [4+2] imine/alkyne annulation
Rajith S. Manan
Pinjing Zhao
Nature Communications, 7
[3] Access to 2-Aroylthienothiazoles via C-H/N-O Bond Functionalization of Oximes
Zhou, Peiqi
Huang, Yubing
Wu, Wanqing
Zhou, Jiaming
Yu, Wentao
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ORGANIC LETTERS, 2019, 21 (24) : 9976 - 9980
[4] Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol
Dang, Xinxin
He, Yu
Liu, Yingtian
Chen, Xuehong
Li, Jun-Long
Zhou, Xian-Li
Jiang, Hezhong
Li, Jiahong
RSC ADVANCES, 2018, 8 (52): : 30050 - 30054
[5] Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes
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Shi, Sijia
Zhang, Wei
Nian, Yong
Wu, Xiaowei
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[6] Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization
Tang, Qiuzheng
Xia, Dexin
Jin, Xiqing
Zhang, Qing
Sun, Xiao-Qiang
Wang, Congyang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) : 4628 - 4631
[7] [4+2] Annulation Cascades of 2-Bromo-1-arylpropan-1-ones with Terminal Alkynes Involving C-Br/C-H Functionalization
Ouyang, Xuan-Hui
Hu, Chao
Song, Ren-Jie
Li, Jin-Heng
ORGANIC LETTERS, 2018, 20 (15) : 4659 - 4662
[8] Rhodium-catalysed regioselective [4+2]-type annulation of 1-H-indazoles with propargyl alcohols: direct access to 6-alkenylindazolo[3,2-a]isoquinolines
Zhao, Xiang
Yue, Xuelin
Han, Zeng
Feng, Yadong
Gao, Ting
Li, Sanshu
Cui, Xiuling
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (20): : 5617 - 5623
[9] Palladium-Catalyzed Tandem Dehydrogenative [4+2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations
Sun, Manman
Chen, Weida
Xia, Xiangyu
Shen, Guodong
Ma, Yongmin
Yang, Jianguo
Ding, Hanfeng
Wang, Zhiming
ORGANIC LETTERS, 2020, 22 (08) : 3229 - 3233
[10] The Rh(iii)-catalysed C-H/N-H annulation of 2-thienyl- and 2-phenyl-quinazolin-4(3H)-ones with diphenylacetylene
Moshkina, Tatyana N.
Nosova, Emiliya V.
Lipunova, Galina N.
Zhilina, Ekaterina F.
Slepukhin, Pavel A.
Nikonov, Igor L.
Charushin, Valery N.
NEW JOURNAL OF CHEMISTRY, 2021, 45 (19) : 8456 - 8466

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