CuOTf-Catalyzed Selective Generation of 2-Aminopyrimidines from Carbodiimides and Diaryliodonium Salts by a Triple C(sp(3))-H Functionalization

doi:10.1002/chem.201604739

	CuOTf-Catalyzed Selective Generation of 2-Aminopyrimidines from Carbodiimides and Diaryliodonium Salts by a Triple C(sp(3))-H Functionalization
	Yan, Haihan 1; Zhang, Wen-Xiong 1,2; Xi, Zhenfeng 1; Chi, Yue 1
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	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.