Gold-catalyzed tandem reaction of o-alkynylphenols with diazo compounds: access to 2,3-disubstituted benzofurans

被引：3
作者：
Huang, Tingzhong [1 ]
Shao, Ying [1 ]
Tang, Shengbiao [1 ]
Sun, Jiangtao [1 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 28期
基金：
中国国家自然科学基金;
关键词：
DERIVATIVES; CYCLIZATION; LIGAND;
D O I：
10.1039/d3ob00893b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A gold-catalyzed tandem reaction of o-alkynylphenols with diazo compounds has been developed, providing the 2,3-disubstituted benzofurans in moderate to good yields under mild reaction conditions. In this protocol, the vinyl gold and gold carbene species might form during the reaction process. Control experiments have been performed to understand the reaction mechanism.
引用
收藏
页码：5752 / 5756
页数：5
相关论文
共 36 条
[1]   Anticancer therapeutic potential of benzofuran scaffolds [J].
Abbas, Ashraf A. ;
Dawood, Kamal M. .
RSC ADVANCES, 2023, 13 (16) :11096-11120
[2]   Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations [J].
Agasti, Soumitra ;
Dey, Aniruddha ;
Maiti, Debabrata .
CHEMICAL COMMUNICATIONS, 2017, 53 (49) :6544-6556
[3]   3-Naphthylindole Construction by Rhodium(II)-Catalyzed Regioselective Direct Arylation of Indoles with 1-Diazonaphthalen-2-(1H)-ones [J].
Baral, Ek Raj ;
Lee, Yong Rok ;
Kim, Sung Hong .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (13) :2883-2892
[4]   Gold-Catalyzed Highly Diastereoselective Oxy-Propargylamination of Allenamides with C-Alkynyl N-Boc N,O-Acetals [J].
Chen, Long ;
Yu, Jianliang ;
Tang, Shengbiao ;
Shao, Ying ;
Sun, Jiangtao .
ORGANIC LETTERS, 2019, 21 (22) :9050-9054
[5]   Design of N-Benzoxaborole Benzofuran GSK8175-Optimization of Human Pharmacokinetics Inspired by Metabolites of a Failed Clinical HCV Inhibitor [J].
Chong, Pek Y. ;
Shotwell, J. Brad ;
Miller, John ;
Price, Daniel J. ;
Maynard, Andy ;
Voitenleitner, Christian ;
Mathis, Amanda ;
Williams, Shawn ;
Pouliot, Jeffrey J. ;
Creech, Katrina ;
Wang, Feng ;
Fang, Jing ;
Zhang, Huichang ;
Tai, Vincent W. -F. ;
Turner, Elizabeth ;
Kahler, Kirsten M. ;
Crosby, Renae ;
Peat, Andrew J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (07) :3254-3267
[6]   Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates [J].
Hashmi, A. Stephen K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5232-5241
[7]   On the Trapping of Vinylgold Intermediates [J].
Hashmi, A. Stephen K. ;
Ramamurthi, Tanuja Dondeti ;
Rominger, Frank .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :971-975
[8]   Gold Catalysis: Isolation of Vinylgold Complexes Derived from Alkynes [J].
Hashmi, A. Stephen K. ;
Schuster, Andreas M. ;
Rominger, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (44) :8247-8249
[9]   Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells [J].
He, Guo-Xue ;
Yuan, Jing-Mei ;
Zhu, Hai-Miao ;
Wei, Kai ;
Wang, Ling-Yun ;
Kong, Shi-Lin ;
Mo, Dong-Liang ;
Pan, Cheng-Xue ;
Su, Gui-Fa .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (08) :1660-1664
[10]   Intramolecular Cyclization of Aryl Propargyl Ethers: A Straightforward and Convenient Approach to Benzofuran Derivatives [J].
Hosseinian, Akram ;
Babazadeh, Mirzaagha ;
Edjlali, Ladan ;
Rahmani, Zahra ;
Vessally, Esmail .
CURRENT ORGANIC SYNTHESIS, 2018, 15 (07) :972-981
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