41780-81-8Relevant academic research and scientific papers
Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application
Sinai, ádám,Simkó, Dániel Cs.,Szabó, Fruzsina,Paczal, Attila,Gáti, Tamás,Bényei, Attila,Novák, Zoltán,Kotschy, András
supporting information, p. 1122 - 1128 (2020/03/03)
Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.
Copper(i)-catalyzed benzylation of triazolopyridine through direct C-H functionalization
Reddy Lonka, Madhava,Zhang, Jinquan,Gogula, Thirupathi,Zou, Hongbin
, p. 7455 - 7460 (2019/08/20)
A general and efficient copper-catalyzed benzylation reaction of triazolopyridine with N-tosylhydrazones was developed. This reaction forms a C(sp2)-C(sp3) bond through cross-coupling, and represents an exceedingly practical method t
Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source
Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng
, p. 7621 - 7627 (2017/07/26)
A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.
Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes
Gao, Yang,Xiong, Wenfang,Chen, Huoji,Wu, Wanqing,Peng, Jianwen,Gao, Yinglan,Jiang, Huanfeng
, p. 7456 - 7467 (2015/08/18)
A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.
Rhodium(III)-catalyzed ortho alkenylation of n-phenoxyacetamides with n-tosylhydrazones or diazoesters through C-H activation
Hu, Fangdong,Xia, Ying,Ye, Fei,Liu, Zhenxing,Ma, Chen,Zhang, Yan,Wang, Jianbo
supporting information, p. 1364 - 1367 (2014/03/21)
A coupling reaction of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through RhIII-catalyzed C-H activation is reported. In this reaction, ortho-alkenyl phenols were obtained in good yields and with excellent regio- and stereoselectivity. Rh-c
Reductive coupling reactions: A new strategy for C(sp3)-P bond formation
Chen, Zi-Sheng,Zhou, Zhao-Zhao,Hua, Hui-Liang,Duan, Xin-Hua,Luo, Jian-Yi,Wang, Jia,Zhou, Ping-Xin,Liang, Yong-Min
supporting information, p. 1065 - 1068 (2013/02/25)
The C(sp3)-P bond forming reaction utilizing N-tosylhydrazones as readily available alkylating reagents was developed, which provides a new opportunity for preparing phosphine oxide derivatives with moderate to good yields. This reductive coupling reaction is proposed to proceed through an insertion of copper carbene into P-H bond of H-phosphorus oxides. The salient features of the reaction are operational simplicity and functional-group tolerance.
Copper-catalyzed direct ortho-alkylation of N-iminopyridinium ylides with N-tosylhydrazones
Xiao, Qing,Ling, Lin,Ye, Fei,Tan, Renchang,Tian, Leiming,Zhang, Yan,Li, Yuxue,Wang, Jianbo
supporting information, p. 3879 - 3885 (2013/05/22)
Copper-catalyzed cross-coupling of N-tosylhydrazones with N-iminopyridinium ylides leads to the direct C-H alkylation. This direct C-H bond alkylation transformation uses inexpensive CuI as the catalyst without any ligand. The reaction is operationally simple and conducted under mild conditions, giving the corresponding alkylated pyridines in moderate to good yields. DFT calculation provides insights into the reaction mechanism, suggesting that the reaction proceeds through the Cu carbene migratory insertion process.
Coupling of n-tosylhydrazones with terminal alkynes catalyzed by copper(i): Synthesis of trisubstituted allenes
Xiao, Qing,Xia, Ying,Li, Huan,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 1114 - 1117 (2011/04/16)
The easy way to allenes: An operationally simple reaction under mild conditions has led to the direct formation of trisubstituted allenes (see scheme; Ts=4-toluenesulfonyl). An unprecedented copper-carbene migratory insertion process seems to take place,
Copper-catalyzed direct benzylation or allylation of 1,3-azoles with N -tosylhydrazones
Zhao, Xia,Wu, Guojiao,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 3296 - 3299 (2011/04/24)
Cu-Catalyzed cross-coupling of N-tosylhydrazones with 1,3-azoles leads to the direct C-H benzylation or allylation. Cu carbene migratory insertion is proposed to play the key role in this transformation.
Copper(I)-catalyzed addition of grignard reagents to in situ-derived N -sulfonyl azoalkenes: An umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers
Hatcher, John M.,Coltart, Don M.
supporting information; experimental part, p. 4546 - 4547 (2010/06/13)
The α-alkylation of N-sulfonyl hydrazones via in situ-derived azoalkenes provides an umpolung approach to ketone α-alkylation that has considerable potential with regard to catalysis and the direct incorporation of functionality not amenable to the use of enolate chemistry. Herein, we describe the first Cu(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes. This method is remarkable in its ability to deliver highly sterically hindered compounds that would be difficult or impossible to synthesize via traditional enolate chemistry, including those having up to three contiguous quaternary centers.
