Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C-H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study
文献类型：期刊论文
| 作者 | Zhao, Fei4; Zhou, Zhi1,2,3; Lu, Yangbin4; Qiao, Jin4; Zhang, Xiaoning4; Gong, Xin4; Liu, Siyu4; Lin, Shuang1,2,3; Wu, Xiaowei5,6; Yi, Wei1,2,3 |
| 刊名 | ACS CATALYSIS
 |
| 出版日期 | 2021-11-19 |
| 卷号 | 11期号:22页码:13921-13934 |
| ISSN号 | 2155-5435 |
| 关键词 | rhodium(III) catalysis C-H activation domino reaction furan-2(5H)-ones 5-hydroxyfuran-2(5H)-ones DFT calculations |
| DOI | 10.1021/acscatal.1c03846 |
| 通讯作者 | Zhao, Fei(zhaofei@cdu.edu.cn) ; Wu, Xiaowei(wuxiaowei@simm.ac.cn) ; Yi, Wei(yiwei@gzhmu.edu.cn) |
| 英文摘要 | Exploring multistep cascade reactions triggered by C-H activation are recognized as appealing, yet challenging. Herein, we disclose a Rh(III)-catalyzed domino C-H coupling of N-carbamoyl indoles and 4-hydroxy-2-alkynoates for the streamlined assembly of highly functionalized furan-2(5H)-ones in which the carbamoyl-directing group (DG) is given a dual role of an auxiliary group and a migrating acylating reagent via the cleavage of stable C-N bonds at room temperature. More importantly, the obtained furan-2(5H)-one skeleton could be further functionalized under air in situ via C5-H hydroxylation by simply switching the solvent or additive, providing fully substituted furan-2(5H)-ones with the installation of an alcohol-based C5 quaternary carbon center. Detailed experimental studies and density functional theory calculations reveal that a Rh(III)-mediated tandem C-H activation/alkyne insertion/DG migration/lactonization accounts for the developed transformation to achieve high functionalities with the observed exclusive selectivity. The potential biological application of the obtained furan-2(5H)-ones as a class of potent PPAR gamma ligands further highlights the synthetic utility of the developed methodology. This protocol is endowed with several salient features including efficient multistep cascade triggered by C-H activation, excellent chemo-, regio-, and stereoselectivity, high bond forming efficiency (e.g., two C-C and two C-O bonds), solvent-or additive-controlled product selectivity, good functional-group compatibility, and mild redox-neutral conditions. |
| WOS关键词 | DIRECTING-GROUP ; BOND FUNCTIONALIZATIONS ; N-PHENOXYACETAMIDES ; TETRASUBSTITUTED ALKENES ; FACILE CONSTRUCTION ; DIVERGENT SYNTHESIS ; ORGANIC-SOLVENTS ; METAL ; ACTIVATION ; OXYGEN |
| 资助项目 | National Natural Science Foundation of China[21602022] ; National Natural Science Foundation of China[21877020] ; 1000 Talents Program of Sichuan Province ; Chengdu Talents Program ; Chenghua District Talents Program ; Science and Technology Program of Sichuan Province[2018JY0345] ; Guangdong Natural Science Funds for Distinguished Young Scholar[2017 A030306031] ; Shanghai Pujiang Program[21PJ1415800] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | AMER CHEMICAL SOC |
| WOS记录号 | WOS:000758012900005 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/300330]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Zhao, Fei; Wu, Xiaowei; Yi, Wei |
| 作者单位 | 1.Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China 2.Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China 3.Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China 4.Chengdu Univ, Sichuan Ind Inst Antibiot, Sch Pharm, Antibiot Res & Re evaluat Key Lab Sichuan Prov, Chengdu 610106, Peoples R China 5.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China 6.Chinese Acad Sci, Shanghai Inst Mat Med, Zhongshan Inst Drug Discovery, Zhongshan 528400, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhao, Fei,Zhou, Zhi,Lu, Yangbin,et al. Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C-H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study[J]. ACS CATALYSIS,2021,11(22):13921-13934. |
| APA | Zhao, Fei.,Zhou, Zhi.,Lu, Yangbin.,Qiao, Jin.,Zhang, Xiaoning.,...&Yi, Wei.(2021).Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C-H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study.ACS CATALYSIS,11(22),13921-13934. |
| MLA | Zhao, Fei,et al."Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C-H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study".ACS CATALYSIS 11.22(2021):13921-13934. |
入库方式： OAI收割
来源：上海药物研究所
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