74993-52-5Relevant articles and documents
An Activity-Based Sensing Fluorogenic Probe for Monitoring Ethylene in Living Cells and Plants
Chen, Yiliang,Guo, Duojing,Jing, Maofeng,Li, Ji,Li, Yu,Liu, Hao,Wang, Biao,Wei, Lirong,Yan, Wei,Ye, Yonghao,Yu, Na,Zhao, Jing,Zheng, Ying
supporting information, p. 21934 - 21942 (2021/08/30)
Ethylene (ET) is an important gaseous plant hormone. It is highly desirable to develop fluorescent probes for monitoring ethylene in living cells. We report an efficient RhIII-catalysed coupling of N-phenoxyacetamides to ethylene in the presenc
Rhodium(III)-Catalyzed Enantio- and Diastereoselective C?H Cyclopropylation of N-Phenoxylsulfonamides: Combined Experimental and Computational Studies
Zheng, Guangfan,Zhou, Zhi,Zhu, Guoxun,Zhai, Shuailei,Xu, Huiying,Duan, Xujing,Yi, Wei,Li, Xingwei
supporting information, p. 2890 - 2896 (2020/01/24)
Cyclopropane rings are a prominent structural motif in biologically active molecules. Enantio- and diastereoselective construction of cyclopropanes through C?H activation of arenes and coupling with readily available cyclopropenes is highly appealing but
Synthesis of ortho-phenolic sulfilimines via an intermolecular sulfur atom transfer cascade reaction
Ren, Yan,Song, Yinan,Xiong, Feng,Xu, Shaojian,Zhang, Linxing,Zhang, Xinhao,Zuo, Yingying
supporting information, p. 3799 - 3803 (2020/06/08)
To expand the toolbox for the synthesis of ortho-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction has a wide substrate scope and can be conducted on a gram scale with excellent reaction efficiency.
Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of N-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C-H/C-C Activations
Pan, Jin-Long,Liu, Chang,Chen, Chao,Liu, Tuan-Qing,Wang, Man,Sun, Zhenliang,Zhang, Shu-Yu
supporting information, p. 2823 - 2827 (2019/04/30)
A cascade [3 + 2] annulation and ring opening of N-aryloxyacetamides with 1-alkynylcyclobutanols via Rh(III)-catalyzed redox-neutral C-H/C-C activations using internal oxidative O-NHAc and -OH as the dual directing groups has been achieved. This reaction provided an efficient and regioselective approach to benzofuran derivatives with good functional group compatibility and high yields.
RhIII-Catalyzed Decarboxylative o-Acylation of Arenes Bearing an Oxidizing Directing Group
Bera, Suvankar,Chandrasekhar,Chatterjee, Satadru,Killi, Sunil Kumar,Sarkar, Debabrata,Banerji, Biswadip
supporting information, p. 3877 - 3881 (2019/06/28)
Here in we report, rhodium(III)-catalyzed decarboxylative acylation of arenes using α-oxocarboxylic acids as acyl surrogate. In this strategy, O–NHAc group act as an autocleavable oxidizing directing group (ODGauto), thus giving rise to ortho-acylated phenols in moderate to good yields. Mechanistic studies provided strong support for a kinetically relevant C–H bond activation. According to the best of our knowledge, this is the first report of Rhodium catalyzed decarboxylative acylation.
Rhodium(III)-catalysed cascade [3 + 2] annulation of: N -aryloxyacetamides with 3-(hetero)arylpropiolic acids: Synthesis of benzofuran-2(3 H)-ones
Pan, Jin-Long,Liu, Tuan-Qing,Chen, Chao,Li, Quan-Zhe,Jiang, Wei,Ding, Tong-Mei,Yan, Zhi-Qiang,Zhu, Guo-Dong
supporting information, p. 8589 - 8600 (2019/10/02)
Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).
Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides
Wu, Yunxiang,Chen, Zhaoqiang,Yang, Yaxi,Zhu, Weiliang,Zhou, Bing
supporting information, p. 42 - 45 (2018/01/17)
A Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C-H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization reactions in an efficient manner.
Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization
Pan, Jin-Long,Chen, Chao,Hao, Yu,Liu, Chang,Bai, He-Yuan,Ding, Jun,Zhang, Shu-Yu,Wang, Li-Ren,Xie, Peipei,Xia, Yuanzhi
supporting information, p. 7131 - 7136 (2018/12/14)
A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.
Combination of Cp*RhIII-Catalyzed C?H Activation and a Wagner–Meerwein-Type Rearrangement
Wang, Xiaoming,Lerchen, Andreas,Gensch, Tobias,Knecht, Tobias,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 1381 - 1384 (2017/01/24)
A combination of Cp*RhIII-catalyzed C?H activation and Wagner–Meerwein-type rearrangement was successfully achieved for the first time. Thus, bridged polycyclic molecules that are not readily accessible by other means were accessed under mild c
Rhodium(III)-Catalyzed Annulative Carbooxygenation of 1,1-Disubstituted Alkenes Triggered by C?H Activation
Li, Yang,Tang, Yuhai,He, Xin,Shi, Dandan,Wu, Jun,Xu, Silong
supporting information, p. 7453 - 7457 (2017/06/06)
A Cp*RhIII-catalyzed annulative carbooxygenation of challenging 1,1-disubstituted alkenes triggered by C?H activation of N-aryloxyacetamides has been established, which affords 2,3-dihydrobenzofuran derivatives with a quaternary carbon center i
