Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides

被引：133

作者：

Cheng, Yannan ^{[1
]}

Gu, Xiangyong ^{[1
]}

Li, Pixu ^{[1
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

关键词：

C-H-ARYLATION; FUNCTIONALIZATION; HETEROARENES; BUTOXIDE;

D O I：

10.1021/ol400946k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)(3) was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway.

引用

页码：2664 / 2667

页数：4

共 23 条

[1] Beller M., 2004, TRANSITION METALS OR
[2] HOMOLYTIC ARYLATION OF AROMATIC AND POLYFLUOROAROMATIC COMPOUNDS
BOLTON, R
WILLIAMS, GH
[J]. CHEMICAL SOCIETY REVIEWS, 1986, 15 (02) : 261 - 289
[3] Room-Temperature Photoinduced Direct C-H-Arylation via Base-Promoted Homolytic Aromatic Substitution
Buden, Maria E.
Guastavino, Javier F.
Rossi, Roberto A.
[J]. ORGANIC LETTERS, 2013, 15 (06) : 1174 - 1177
[4] Aerobic Visible-Light Photoredox Radical C-H Functionalization: Catalytic Synthesis of 2-Substituted Benzothiazoles
Cheng, Yannan
Yang, Jun
Qu, Yue
Li, Pixu
[J]. ORGANIC LETTERS, 2012, 14 (01) : 98 - 101
[5] Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts
Hari, Durga Prasad
Schroll, Peter
Koenig, Burkhard
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) : 2958 - 2961
[6] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
Hassan, J
Sévignon, M
Gozzi, C
Schulz, E
Lemaire, M
[J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1359 - 1469
[7] Room-Temperature C-H Arylation: Merger of Pd-Catalyzed C-H Functionalization and Visible-Light Photocatalysis
Kalyani, Dipannita
McMurtrey, Kate B.
Neufeldt, Sharon R.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (46) : 18566 - 18569
[8] Visible-Light-Induced Photocatalytic Reductive Transformations of Organohalides
Kim, Hyejin
Lee, Chulbom
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) : 12303 - 12306
[9] Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C-H Arylation of Unactivated Benzene
Liu, Wei
Cao, Hao
Zhang, Hua
Zhang, Heng
Chung, Kin Ho
He, Chuan
Wang, Haibo
Kwong, Fuk Yee
Lei, Aiwen
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) : 16737 - 16740
[10] Room-Temperature Arylation of Arenes and Heteroarenes with Diaryliodonium Salts by Photoredox Catalysis
Liu, Yu-Xia
Xue, Dong
Wang, Jia-Di
Zhao, Cong-Jun
Zou, Qing-Zhu
Wang, Chao
Xiao, Jianliang
[J]. SYNLETT, 2013, 24 (04) : 507 - 513

← 1 2 3 →