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![]() ![]() ![]() | |
刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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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. |
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