5667-64-1Relevant academic research and scientific papers
Cu-Catalyzed oxidative 3-amination of indoles via formation of indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
Watanabe, Kazuhiro,Moriyama, Katsuhiko
, (2019)
An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. o-Alkoxy(diacetoxyiodo)arenes showed higher reactivity in the reaction than o-alkyl(diacetoxyiodo)arenes, efficiently promoting the formation of indolyl(aryl)iodonium imides in the first step.
Copper-Catalyzed Indole-Selective C-N Coupling Reaction of Indolyl(2-alkoxy-phenyl)iodonium Imides: Effect of Substituent on Iodoarene as Dummy Ligand
Watanabe, Kazuhiro,Moriyama, Katsuhiko
, p. 14827 - 14833 (2019/01/03)
A monoalkoxy phenyl group as a dummy ligand on indolyl(aryl)iodonium imides, which is related to the N-I bonding hypervalent iodine(III) compound, for the copper-catalyzed indole-selective C-N coupling reaction was designed to provide 3-bissulfonimido-ind
Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes
Youn, So Won,Ko, Tae Yun,Jang, Young Ho
supporting information, p. 6636 - 6640 (2017/05/29)
A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles.
Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
, p. 8010 - 8019 (2015/03/18)
The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
Nickel-Catalyzed Desulfitative Suzuki-Miyaura Cross-Coupling of N,N-Disulfonylmethylamines and Arylboronic Acids
Chen, Liangshun,Lang, Hongyue,Fang, Lei,Yu, Jianjun,Wang, Limin
supporting information, p. 6385 - 6389 (2016/02/18)
A nickel-catalyzed approach for the synthesis of biaryl compounds from N,N-disulfonylmethylamines and arylboronic acids has been developed. Instead of arenesulfonyl chlorides, various N,N-disulfonylmethylamines were used as the aryl source through extrusion of SO2 to give cross-coupling products in moderate to good yields. A NiCl2(dppp)-catalyzed [dppp = 1,3-bis(diphenylphosphino)propane] desulfitative Suzuki-Miyaura cross-coupling reaction between N,N-disulfonylmethylamines and arylboronic acids is described for the first time. The biaryl compounds are obtained in moderate to good yields.
Nickel-catalyzed one-pot Suzuki-Miyaura cross-coupling of phenols and arylboronic acids mediated by N,N-ditosylaniline
Chen, Liangshun,Lang, Hongyue,Fang, Lei,Zhu, Mengyun,Liu, Jinqian,Yu, Jianjun,Wang, Limin
supporting information, p. 4953 - 4957 (2014/08/18)
An efficient method for the construction of two distinct C aryl-Caryl bonds through the Ni-catalyzed Suzuki-Miyaura cross-coupling of phenols with arylboronic acids has been developed. This reaction proceeds through the in situ tosylation of phenols by using N,N-ditosylaniline as the sulfonylating reagent, which is highly active, markedly stable, and easily prepared. The scope with respect to the coupling partners - phenols and boronic acids - is broad, and sensitive functional groups are tolerated. Phenols, especially those containing an unprotected amino group, which are generally problematic for coupling under conventional one-pot conditions, are also viable substrates in this transformation.
