93729-09-0Relevant articles and documents
Sequential C-S and S-N Coupling Approach to Sulfonamides
Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 1841 - 1845 (2020/03/04)
A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
supporting information, p. 13481 - 13494 (2020/12/15)
Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
Rearrangement Reaction Based on the Structure of N-Fluoro- N-alkyl Benzenesulfonamide
Wang, Han-Ying,Pu, Xiao-Qiu,Yang, Xian-Jin
, p. 13103 - 13110 (2018/10/20)
A novel rearrangement reaction based on the structure of N-fluoro-N-alkyl benzenesulfonamide was developed. The reaction proceeded readily at 50 °C in formic acid and generated a variety of benzenesulfonamides and aldehydes or ketones simultaneously. The reaction mechanism is believed to be a concerted mechanism that consist of 1,2-aryl migration with the departure of fluorine anion via an SN2 mechanism. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operations, and a broad substrate scope.
Transition-metal-free and organic solvent-free conversion of N-substituted 2-aminobiaryls into corresponding carbazoles via intramolecular oxidative radical cyclization induced by peroxodisulfate
Natarajan, Palani,Priya,Chuskit, Deachen
supporting information, p. 5854 - 5861 (2017/12/26)
An atom-economical and environmentally benign approach for the synthesis of N-substituted carbazoles from analogous 2-aminobiaryls using peroxodisulfate in water is reported. The reactions proceeded through an intramolecular oxidative radical cyclization
Palladium-catalyzed oxidative insertion of carbon monoxide to N -sulfonyl-2-aminobiaryls through C-H bond activation: Access to bioactive phenanthridinone derivatives in one pot
Rajeshkumar, Venkatachalam,Lee, Tai-Hua,Chuang, Shih-Ching
, p. 1468 - 1471 (2013/06/26)
Palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C-H bond activation and C-C, C-N bond formation under TFA-free and milder conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important phenanthridinone derivatives in yields up to 94%.
Palladium-catalyzed and hybrid acids-assisted synthesis of [60]fulleroazepines in one pot under mild conditions: Annulation of N-sulfonyl-2-aminobiaryls with [60]fullerene through sequential C-H bond activation, C-C and C-N bond formation
Rajeshkumar, Venkatachalam,Chan, Fu-Wei,Chuang, Shih-Ching
, p. 2473 - 2483,11 (2020/08/31)
An extraordinarily efficient hybrid acids-assisted, palladium-catalyzed and chelating-group-assisted C-H bond activation of N-sulfonyl-2-aminobiaryls and their annulations with [60]fullerene via sequential C-C and C-N bond formation at room temperature to
Intramolecular oxidative C-N bond formation for the synthesis of carbazoles: Comparison of reactivity between the copper-catalyzed and metal-free conditions
Cho, Seung Hwan,Yoon, Jungho,Chang, Sukbok
, p. 5996 - 6005 (2011/06/11)
New synthetic procedures for intramolecular oxidative C-N bond formation have been developed for the preparation of carbazoles starting from N-substituted amidobiphenyls under either Cu-catalyzed or metal-free conditions using hypervalent iodine(III) as an oxidant. Whereas iodobenzene diacetate or bis(trifluoroacetoxy)iodobenzene alone undergoes the reaction to provide carbazole products in moderate to low yields, combined use of copper(II) triflate and the iodine(III) species significantly improves the reaction efficiency, giving a more diverse range of products in good to excellent yields. On the basis of mechanistic studies including kinetic profile, isotope effects, and radical inhibition experiments, the copper species is proposed to catalytically activate the hypervalent iodine(III) oxidants. The synthetic utility of the present approach was nicely demonstrated in a direct synthesis of indolo[3,2-b]carbazole utilizing a double C-N bond formation.
Pd-catalyzed sequential C-C and C-N bond formations for the synthesis of N-heterocycles: Exploiting protecting group-directed C-H activation under modified reaction conditions
Kim, Byung Seok,Lee, Sun Young,Youn, So Won
supporting information; experimental part, p. 1952 - 1957 (2011/11/04)
Easy & efficient: A Pd-catalyzed domino olefination/conjugate addition reaction of N-Ts-2-arylanilines with activated olefins has been achieved at ambient temperature under the newly defined reaction conditions. This process highlighted the directing effect of the N-protecting group in C-H activation, displayed broad substrate scope with wide functional group compatibility; thus rendering a straightforward entry to a wide variety of N-heterocycles such as dihydrophenanthridines.
Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation
Tsang, W. C. Peter,Munday, Rachel H.,Brasche, Gordon,Zheng, Nan,Buchwald, Stephen L.
, p. 7603 - 7610 (2008/12/22)
(Chemical Equation Presented) The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.
Oxidative Cross-Coupling of N-(2′-Phenylphenyl)benzene-sulfonamides or Benzoic and Naphthoic Acids with Alkenes Using a Palladium-Copper Catalyst System under Air
Miura, Masahiro,Tsuda, Takatoshi,Satoh, Tetsuya,Pivsa-Art, Sommai,Nomura, Masakatsu
, p. 5211 - 5215 (2007/10/03)
N-(2′-Phenylphenyl)benzenesulfonamides react with acrylate esters accompanied via cleavage of the C-H bond at their 2′-position in the presence of a catalyst system of Pd(OAc)2 and Cu(OAc)2 and a base under air to produce 5,6-dihydro-5-(benzenesulfonyl)phenanthridine-6-acetate derivatives in high yields. The reactions of benzoic acid with butyl acrylate and styrene can also give 3-[(butoxycarbonyl)methyl]phthalide and 3-phenylisocoumarin, respectively.
