RhIII-catalyzed dual directing group assisted sterically hindered C-H bond activation: a unique route to meta and ortho substituted benzofurans

被引：36

作者：

Yeh, Chien-Hung ^{[1
]}

Chen, Wei-Chen ^{[1
]}

Gandeepan, Parthasarathy ^{[1
]}

Hong, Ya-Chun ^{[1
]}

Shih, Cheng-Hung ^{[1
]}

Cheng, Chien-Hong ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 45期

关键词：

INTERNAL ALKYNES; ISOQUINOLINIUM SALTS; EFFICIENT SYNTHESIS; ARYL HALIDES; ANNULATION; PHENOLS; DERIVATIVES; CYCLIZATION; ARENES; INDOLES;

D O I：

10.1039/c4ob01876a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for the synthesis of highly substituted benzofurans from meta-substituted hydroxybenzenes and alkynes via a rhodium(III)-catalyzed activation of a sterically hindered C-H bond is demonstrated. A possible mechanism involving dual directing group assisted ortho C-H bond activation is proposed.

引用

页码：9105 / 9108

页数：4

共 50 条

[31] Regioselective Synthesis of 4-Substituted Indoles via C-H Activation: A Ruthenium Catalyzed Novel Directing Group Strategy
Lanke, Veeranjaneyulu
Prabhu, Kandikere Ramaiah
ORGANIC LETTERS, 2013, 15 (24) : 6262 - 6265
[32] Annulation of β-Enaminonitriles with Alkynes via RhIII-Catalyzed C-H Activation: Direct Access to Highly Substituted 1-Naphthylamines and Naphtho[1,8-bc]pyridines
Wang, Haili
Xu, Hong
Li, Bin
Wang, Baiquan
ORGANIC LETTERS, 2018, 20 (18) : 5640 - 5643
[33] Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C-H bond activation
Yamakawa, Takeshi
Yoshikai, Naohiko
TETRAHEDRON, 2013, 69 (22) : 4459 - 4465
[34] Theoretical study on the mechanism of palladium-catalyzed sp2 C-H bond activation using cyano as a directing group
Ren, Ying
Yan, Chao
Jia, Jianfeng
Wu, Hai-Shun
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 824 : 88 - 98
[35] Palladium-Catalyzed Alkenylation via sp2 C-H Bond Activation Using Phenolic Hydroxyl as the Directing Group
Zhang, Chun
Ji, Jing
Sun, Peipei
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07): : 3200 - 3205
[36] Ruthenium-Catalyzed Selective Aerobic Oxidative ortho-Alkenylation of Substituted Phenols with Alkenes through C-H Bond Activation
Reddy, Mallu Chenna
Jeganmohan, Masilamani
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (06) : 1150 - 1157
[37] Synthesis of naphthalene-substituted aromatic esters via Rh(iii)-catalyzed C-H bond naphthylation and cascade directing group transformation
Cui, Yue
Li, Siyu
Wang, Hesheng
Zeng, Jing
Wang, Yichen
Bu, Xiubin
Yang, Xiaobo
Zhao, Zhen
CHEMICAL COMMUNICATIONS, 2022, 58 (95) : 13230 - 13233
[38] Direct Ortho Arylation of 9-(Pyridin-2-yl)-9H-carbazoles Bearing a Removable Directing Group via Palladium(II)-Catalyzed C-H Bond Activation
Chu, Jean-Ho
Wu, Chung-Chiu
Chang, Deng-Hsiang
Lee, Ya-Ming
Wu, Ming-Jung
ORGANOMETALLICS, 2013, 32 (01) : 272 - 282
[39] Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines
Chinnagolla, Ravi Kiran
Pimparkar, Sandeep
Jeganmohan, Masilamani
ORGANIC LETTERS, 2012, 14 (12) : 3032 - 3035
[40] Palladium-Catalyzed Highly Selective ortho-Halogenation (I, Br, Cl) of Arylnitriles via sp2 C-H Bond Activation Using Cyano as Directing Group
Du, Bingnan
Jiang, Xiaoqing
Sun, Peipei
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06): : 2786 - 2791

← 1 2 3 4 5 →