190071-25-1Relevant academic research and scientific papers
Characterization of heterogeneous aryl-Pd(ii)-oxo clusters as active species for C-H arylation
Shin, Taeil,Kim, Minjun,Jung, Younjae,Cho, Sung June,Kim, Hyunwoo,Song, Hyunjoon
supporting information, p. 14404 - 14407 (2020/12/01)
C-H arylation with heterogeneous palladium was investigated. The surface oxidation of Pd nanoparticles with a hypervalent iodine reagent, [Ph2I]BF4, resulted in the generation of Pd(ii)-aryl-oxo clusters, which were characterized as the crucial intermediate.
Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
, p. 3294 - 3299 (2020/01/21)
A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
Palladium/Copper Cocatalyzed Coupling Reaction of Aroyl Hydrazides with Indoles
Liu, Congrong,Yang, Fulai
supporting information, p. 1213 - 1217 (2016/12/28)
An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.
Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides
Liu, Congrong,Ding, Lianghui,Guo, Guang,Liu, Weiwei,Yang, Fu-Lai
, p. 2824 - 2827 (2016/03/12)
A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.
A Scalable Method for Regioselective 3-Acylation of 2-Substituted Indoles under Basic Conditions
Johansson, Henrik,Urruticoechea, Andoni,Larsen, Inna,Sejer Pedersen, Daniel
, p. 471 - 481 (2015/08/25)
Privileged structures such as 2-arylindoles are recurrent molecular scaffolds in bioactive molecules. We here present an operationally simple, high yielding and scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions
Synthesis of 2-Substituted Indoles through Visible Light-Induced Photocatalytic Cyclizations of Styryl Azides
Xia, Xu-Dong,Xuan, Jun,Wang, Qiang,Lu, Liang-Qiu,Chen, Jia-Rong,Xiao, Wen-Jing
, p. 2807 - 2812 (2016/02/18)
A visible light-induced photocatalytic intramolecular cyclization of styryl azides has been developed in the presence of the ruthenium complex Ru(bpy)3Cl2 (0.5 mol%) as photocatalyst at room temperature. The present photocatalytic strategy features operational simplicity as well as high functional group tolerance, and provides a facile access to various 2-substituted N-free indoles in good to excellent yields. Importantly, the present process can employ sunlight as the light source to afford the corresponding products without loss of reaction efficiency.
Copper catalysed domino decarboxylative cross coupling-cyclisation reactions: Synthesis of 2-arylindoles
Ponpandian, Thanasekaran,Muthusubramanian, Shanmugam
, p. 4248 - 4252 (2012/08/28)
The efficient synthesis of 2-arylindoles and 6H-isoindolo[2,1-a]indol-6-one through copper catalysed domino sp-sp2 decarboxylative cross-coupling and subsequent cyclisation reactions of arylpropiolic acids with 2-iodotrifluoroacetanilide has been described. This methodology also demonstrates that indolo[1,2-c]quinazolin-6(5H)-one can be obtained with the elimination of trifluoromethyl anion.
"on water" direct and site-selective Pd-catalysed C-H arylation of (NH)-indoles
Joucla, Lionel,Batail, Nelly,Djakovitch, Laurent
supporting information; experimental part, p. 2929 - 2936 (2011/02/22)
This communication describes the development of a versatile catalytic system based on palladium(II) acetate/bis(diphenylphosphino)methane [Pd(OAc)2/dppm] that works "on water" giving site-selective C-H arylation of (NH)-indoles without protecting or directing groups. Remarkably, the control of regioselectivity was achieved by small changes in the "extra-catalytic" base/halide partners. These innovative methodologies allow a high-yielding access to both C2 and C3-arylindoles, as well as 2,3-diarylindoles, and display high chemo/regioselectivities and structural versatility with regard to either indole or aryl moieties. Copyright
BIS-(SULFONYLAMINO) DERIVATIVES IN THERAPY 065
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Page/Page column 67, (2009/05/28)
The invention provides compounds of formula wherein R1, R2, R3, A and m are as defined in the specification and optical isomers, racemates and tautomers thereof, and pharmaceutically acceptable salts thereof; together with processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds are inhibitors of microsomal prostaglandin E synthase-1
Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus
Ambrus, Joseph I.,Kelso, Michael J.,Bremner, John B.,Ball, Anthony R.,Casadei, Gabriele,Lewis, Kim
scheme or table, p. 4294 - 4297 (2009/04/06)
The synthesis of 22 2-aryl-1H-indoles, including 12 new compounds, has been achieved via Pd- or Rh-mediated methodologies, or selective electrophilic substitution. All three methods were based on elaborations from simple indole precursors. SAR studies on
