Redox-Neutral Rhodium-Catalyzed C-H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp(3))-H/C(sp(2))-H Activation and Oxygen-Atom Transfer

doi:10.1002/anie.201505302

	Redox-Neutral Rhodium-Catalyzed C-H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp(3))-H/C(sp(2))-H Activation and Oxygen-Atom Transfer
	Zhou, Bing2 ; Chen, Zhaoqiang 1; Yang, Yaxi2 ; Ai, Wen 2; Tang, Huanyu 2; Wu, Yunxiang 2; Zhu, Weiliang1 ; Li, Yuanchao 2
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2015-10-05
卷号	54 期号:41 页码:12121-12126
关键词	C-H activation density functional calculations heterocycles nitrogen oxides rhodium
ISSN号	1433-7851
DOI	10.1002/anie.201505302
文献子类	Article
英文摘要	An unprecedented rhodium(III)-catalyzed regioselective redox-neutral annulation reaction of 1-naphthylamine N-oxides with diazo compounds was developed to afford various biologically important 1H-benzo[g] indolines. This coupling reaction proceeds under mild reaction conditions and does not require external oxidants. The only by-products are dinitrogen and water. More significantly, this reaction represents the first example of dual functiaonalization of unactivated a primary C(sp(3))-H bond and C(sp(2))-H bond with diazocarbonyl compounds. DFT calculations revealed that an intermediate iminium is most likely involved in the catalytic cycle. Moreover, a rhodium(III)-catalyzed coupling of readily available tertiary aniline N-oxides with alpha-diazomalonates was also developed under external oxidant-free conditions to access various aminomandelic acid derivatives by an O-atom-transfer reaction.
资助项目	National Natural Science Foundation of China[21302200]
WOS关键词	O HYDROGEN-BONDS ; DIRECT ARYLATION ; CARBENOID FUNCTIONALIZATION ; RH(III)-CATALYZED SYNTHESIS ; ROOM-TEMPERATURE ; ALKYNES ; RH ; ALKENYLATION ; DERIVATIVES ; CLEAVAGE
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000363396000042
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276369]
专题	药物化学研究室药物发现与设计中心
通讯作者	Zhou, Bing
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Medica, Drug Discovery & Design Ctr, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, Dept Med Chem, Shanghai 201203, Peoples R China;
推荐引用方式 GB/T 7714	Zhou, Bing,Chen, Zhaoqiang,Yang, Yaxi,et al. Redox-Neutral Rhodium-Catalyzed C-H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp(3))-H/C(sp(2))-H Activation and Oxygen-Atom Transfer[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2015,54(41):12121-12126.
APA	Zhou, Bing.,Chen, Zhaoqiang.,Yang, Yaxi.,Ai, Wen.,Tang, Huanyu.,...&Li, Yuanchao.(2015).Redox-Neutral Rhodium-Catalyzed C-H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp(3))-H/C(sp(2))-H Activation and Oxygen-Atom Transfer.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,54(41),12121-12126.
MLA	Zhou, Bing,et al."Redox-Neutral Rhodium-Catalyzed C-H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp(3))-H/C(sp(2))-H Activation and Oxygen-Atom Transfer".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54.41(2015):12121-12126.