Rh(III)-Catalyzed Synthesis of 2-Nitro-2H -azirines via sp3 C-H Activation

被引:2
作者
Huang, Xiaojun [1 ]
Ge, Yun [2 ]
Qian, Yang [3 ]
Zhang, Zhengyu [3 ]
机构
[1] Nanjing Tech Univ, Coll Mat Sci & Engn, Nanjing 211816, Peoples R China
[2] Nanjing Tech Univ, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Peoples R China
[3] Nanjing Tech Univ, Coll Food Sci & Light Ind, Nanjing 211816, Peoples R China
关键词
Rh(III); 2-nitro-2H-azirine; derivatives; beta-nitrooxime; sp(3) C-H; RING CONTRACTION; INDOLE SYNTHESIS; 2H-AZIRINES; BOND; CYCLOADDITION; EXPANSION; FUNCTIONALIZATION; AMIDATION; ALKYNES;
D O I
10.1055/a-1804-7546
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expedient Rh(III)-catalytic method has been described to synthesis of 2-nitro-2H-azirine derivatives from easily accessible beta-nitrooxime ethers via sp(3) C-H activation process. This protocol features of low catalyst loading, very mild reaction conditions, and tolerating a diverse of functionalities in good yields. A possible reaction pathway is proposed involving [RhCp*Cl-2](2)-catalyzed sp(3) C-H bond activation and pivalic acid elimination steps.
引用
收藏
页码:969 / 972
页数:4
相关论文
共 44 条
[1]   Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization [J].
Achar, Tapas Kumar ;
Maiti, Sudip ;
Jana, Sadhan ;
Maiti, Debabrata .
ACS CATALYSIS, 2020, 10 (23) :13748-13793
[2]   Rh(III) and Ir(III)Cp* Complexes Provide Complementary Regioselectivity Profiles in Intermolecular Allylic C-H Amidation Reactions [J].
Burman, Jacob S. ;
Harris, Robert J. ;
Farr, Caitlin M. B. ;
Bacsa, John ;
Blakey, Simon B. .
ACS CATALYSIS, 2019, 9 (06) :5474-5479
[3]   Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds [J].
Chen, Xun ;
Xie, Ying ;
Xiao, Xinsheng ;
Li, Guoqiang ;
Deng, Yuanfu ;
Jiang, Huanfeng ;
Zeng, Wei .
CHEMICAL COMMUNICATIONS, 2015, 51 (83) :15328-15331
[4]   2H-Azirines as Potential Bifunctional Chemical Linkers of Cysteine Residues in Bioconjugate Technology [J].
Chen, Yang ;
Yang, Wenjie ;
Wu, Jiamin ;
Sun, Wangbin ;
Loh, Teck-Peng ;
Jiang, Yaojia .
ORGANIC LETTERS, 2020, 22 (05) :2038-2043
[5]   Zinc-Enabled Annulation of Trifluorodiazoethane with 2H-Azirines to Construct Trifluoromethyl Pyrazolines, Pyrazoles, and Pyridazines [J].
Chen, Yue-Ji ;
Zhang, Fa-Guang ;
Ma, Jun-An .
ORGANIC LETTERS, 2021, 23 (15) :6062-6066
[6]   Hoveyda-Grubbs II Catalyst: A Useful Catalyst for One-Pot Visible-Light-Promoted Ring Contraction and Olefin Metathesis Reactions [J].
Ge, Yun ;
Sun, Wangbin ;
Pei, Bingbing ;
Ding, Jia ;
Jiang, Yaojia ;
Loh, Teck-Peng .
ORGANIC LETTERS, 2018, 20 (09) :2774-2777
[7]   Mild metal-catalyzed C-H activation: examples and concepts [J].
Gensch, T. ;
Hopkinson, M. N. ;
Glorius, F. ;
Wencel-Delord, J. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) :2900-2936
[8]   Rh(iii)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion [J].
Ghosh, Bidhan ;
Bera, Satabdi ;
Ghosh, Pintu ;
Samanta, Rajarshi .
CHEMICAL COMMUNICATIONS, 2021, 57 (97) :13134-13137
[9]   Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity [J].
Giri, Ramesh ;
Shi, Bing-Feng ;
Engle, Keary M. ;
Maugel, Nathan ;
Yu, Jin-Quan .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3242-3272
[10]   The Mechanism of Rhodium-Catalyzed Allylic C-H Amination [J].
Harris, Robert J. ;
Park, Jiyong ;
Nelson, Taylor A. F. ;
Iqbal, Nafees ;
Salgueiro, Daniel C. ;
Bacsa, John ;
MacBeth, Cora E. ;
Baik, Mu-Hyun ;
Blakey, Simon B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) :5842-5851