CuOTf-Catalyzed Selective Generation of 2-Aminopyrimidines from Carbodiimides and Diaryliodonium Salts by a Triple C(sp(3))-H Functionalization | |
Yan, Haihan1; Zhang, Wen-Xiong1,2; Xi, Zhenfeng1; Chi, Yue1 | |
刊名 | CHEMISTRY-A EUROPEAN JOURNAL
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2017 | |
卷号 | 23期号:4页码:757-761 |
关键词 | 2-aminopyrimidines c(Sp(3))-h Functionalization Carbodiimide Diaryliodonium Salts Hydrogen Shift |
ISSN号 | 0947-6539 |
DOI | 10.1002/chem.201604739 |
文献子类 | Article |
英文摘要 | The selective C(sp(3))-H bond functionalization is an ideal and atom-economical method in organic synthesis. In this work, 2-aminopyrimidines are generated from a Cu-catalyzed reaction between carbodiimides and diaryliodonium salts, by cleavage of four C(sp(3))-H, one C-N, and one C=N bonds in the carbodiimides. It is the first triple C(sp(3))-H bond functionalization neighboring a C=N bond. The selective synthesis of 2-aminopyrimidines is controlled by the amount of the diaryliodonium salts. The novel mechanism involving a C-N formation/1,5-H shift/1,7-H shift/6 pi-electrocyclic ring-closing/aromatization is well elucidated by the detection of important intermediates and DFT calculations. |
WOS关键词 | C-H FUNCTIONALIZATION ; DIRECT BETA-ARYLATION ; ONE-POT SYNTHESIS ; 1,1,3-TRIARYL-2-AZAALLYL ANIONS ; REGIOSELECTIVE ARYLATION ; BOND FUNCTIONALIZATION ; CASCADE ANNULATION ; DIRECTING GROUPS ; ACTIVATION ; ALKYNES |
WOS研究方向 | Chemistry |
语种 | 英语 |
出版者 | WILEY-V C H VERLAG GMBH |
WOS记录号 | WOS:000395752500003 |
内容类型 | 期刊论文 |
源URL | [http://cas-ir.dicp.ac.cn/handle/321008/169552] ![]() |
专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
通讯作者 | Zhang, Wen-Xiong; Xi, Zhenfeng |
作者单位 | 1.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, BNLMS, Minist Educ,Coll Chem, Beijing 100871, Peoples R China 2.Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China |
推荐引用方式 GB/T 7714 | Yan, Haihan,Zhang, Wen-Xiong,Xi, Zhenfeng,et al. CuOTf-Catalyzed Selective Generation of 2-Aminopyrimidines from Carbodiimides and Diaryliodonium Salts by a Triple C(sp(3))-H Functionalization[J]. CHEMISTRY-A EUROPEAN JOURNAL,2017,23(4):757-761. |
APA | Yan, Haihan,Zhang, Wen-Xiong,Xi, Zhenfeng,&Chi, Yue.(2017).CuOTf-Catalyzed Selective Generation of 2-Aminopyrimidines from Carbodiimides and Diaryliodonium Salts by a Triple C(sp(3))-H Functionalization.CHEMISTRY-A EUROPEAN JOURNAL,23(4),757-761. |
MLA | Yan, Haihan,et al."CuOTf-Catalyzed Selective Generation of 2-Aminopyrimidines from Carbodiimides and Diaryliodonium Salts by a Triple C(sp(3))-H Functionalization".CHEMISTRY-A EUROPEAN JOURNAL 23.4(2017):757-761. |
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