Silver(I)-Catalyzed Enyne Cyclization/Aromatization of Alkyne-Tethered Cyclohexadienones to Access Meta-Substituted Phenols

被引：16
作者：
Munakala, Anandarao [1 ,2 ]
Chegondi, Rambabu [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol CSIR IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 02期
关键词：
CATALYZED AEROBIC DEHYDROGENATION; C-O BOND; HYDROXYLATION; OXYGENATION; DERIVATIVES; 1,6-ENYNES; OXIDATION; ARYLATION; ROUTE; CYCLOISOMERIZATION;
D O I：
10.1021/acs.orglett.0c03819
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein we report a highly regioselective silver(I)-catalyzed intramolecular annulation of alkyne-tethered cyclohexadienones to access meta-substituted phenols with enone functionality, which are difficult to synthesize from conventional methods. The reaction proceeds via intramolecular 1,6-enyne cyclization followed by aromatization and subsequent oxetene ring rearrangement. This strategy has also been compatible with a wide range of C-tethered cyclohexadienones to afford indanes in high yields. The unique functionality of products allows further transformations to expand the diversity.
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收藏
页码：317 / 323
页数：7
相关论文
共 73 条
[31]   Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary [J].
Li, Xin ;
Liu, Yan-Hua ;
Gu, Wen-Jia ;
Li, Bo ;
Chen, Fa-Jie ;
Shi, Bing-Feng .
ORGANIC LETTERS, 2014, 16 (15) :3904-3907
[32]   Efficient Nazarov cyclizations of 2-alkoxy-1,4-pentadien-3-ones [J].
Liang, GX ;
Gradl, SN ;
Trauner, D .
ORGANIC LETTERS, 2003, 5 (26) :4931-4934
[33]   A highly efficient metal-free approach to meta- and multiple-substituted phenols via a simple oxidation of cyclohexenones [J].
Liang, Yu-Feng ;
Song, Song ;
Ai, Lingsheng ;
Li, Xinwei ;
Jiao, Ning .
GREEN CHEMISTRY, 2016, 18 (24) :6462-6467
[34]   Ligand-Promoted Pd-Catalyzed Oxime Ether Directed C-H Hydroxylation of Arenes [J].
Liang, Yu-Feng ;
Wang, Xiaoyang ;
Yuan, Yizhi ;
Liang, Yujie ;
Li, Xinyao ;
Jiao, Ning .
ACS CATALYSIS, 2015, 5 (10) :6148-6152
[35]   Room-Temperature Copper-Catalyzed Oxidation of Electron-Deficient Arenes and Heteroarenes Using Air [J].
Liu, Qiang ;
Wu, Pan ;
Yang, Yuhong ;
Zeng, Ziqi ;
Liu, Jie ;
Yi, Hong ;
Lei, Aiwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (19) :4666-4670
[36]   Overriding Ortho-Para Selectivity via a Traceless Directing Group Relay Strategy: The Meta-Selective Arylation of Phenols [J].
Luo, Junfei ;
Preciado, Sara ;
Larrosa, Igor .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4109-4112
[37]  
MacLellan P., 2014, Nat. Chem, V6, P375, DOI [10.1038/nchem.1941, DOI 10.1038/NCHEM.1941]
[38]   C-H activation/borylation/oxidation: A one-pot unified route to meta-substituted phenois bearing ortho-/para-directing groups [J].
Maleczka, RE ;
Shi, F ;
Holmes, D ;
Smith, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7792-7793
[39]   Palladium-catalyzed C-O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C-O bond in diaryl ethers [J].
Mann, G ;
Incarvito, C ;
Rheingold, AL ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3224-3225
[40]   Rhodium(III)-Catalyzed Meta-Selective C-H Alkenylation of Phenol Derivatives [J].
Mi, Rui-Jie ;
Sun, Yong-Zhen ;
Wang, Jing-Yun ;
Sun, Jing ;
Xu, Zhaoqing ;
Zhou, Ming-Dong .
ORGANIC LETTERS, 2018, 20 (17) :5126-5129
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