72844-84-9Relevant academic research and scientific papers
Aerobic waste-minimized Pd-catalysed C-H alkenylation in GVL using a tube-in-tube heterogeneous flow reactor
Anastasiou, Ioannis,Carpisassi, Luigi,Ferlin, Francesco,Vaccaro, Luigi
supporting information, p. 6576 - 6582 (2021/09/10)
Herein we report the design and application of a tube-in-tube packed-bed flow reactor for the first time for the development of a heterogeneous palladium catalysed oxidative C-C bond formation process. In particular, we have defined an innovative tube-in-
DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
Zhang, Jingran,Li, Xiaoxian,Li, Xuemin,Shi, Haofeng,Sun, Fengxia,Du, Yunfei
supporting information, p. 460 - 463 (2021/01/25)
The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.
Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
Hari Babu, Madala,Ranjith Kumar, Gadi,Kant, Ruchir,Sridhar Reddy, Maddi
supporting information, p. 3894 - 3897 (2017/04/04)
Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.
Cyclodextrin-Grafted Silica-Supported Pd Nanoparticles: An Efficient and Versatile Catalyst for Ligand-Free C-C Coupling and Hydrogenation
Martina, Katia,Baricco, Francesca,Caporaso, Marina,Berlier, Gloria,Cravotto, Giancarlo
, p. 1176 - 1184 (2016/04/05)
Silica is an extremely versatile support, which is capable of hosting metal nanoparticles (NPs) and enhancing their stability and reactivity. In this study, a novel cyclodextrin/silica support for Pd NPs, which we have denoted Pd/Si-CD, has been prepared. The highly efficient and homogeneous impregnation of small palladium nanoparticles on this support has been carried out under conventional conditions, and ultrasound irradiation has been shown to have a beneficial effect on catalyst preparation. The catalyst exhibited excellent activity in ligand-free C-C Suzuki and Heck couplings with a large number of aryl iodide and bromides, in which microwave irradiation use cuts down reaction time. Pd/Si-CD have shown high activity and selectivity in the hydrogenation reaction, and the semihydrogenation of phenyl acetylene was also studied with excellent results.
Rhodium(III)-catalyzed internal oxidative coupling of N-hydroxyanilides with alkenes via C-H activation
Wen, Jing,Wu, An,Chen, Pei,Zhu, Jin
, p. 5282 - 5286 (2015/08/26)
Abstract Described herein is an efficient new method for ortho-olefination of anilides in the presence of AgSbF6 and NaOAc via rhodium(III)-catalyzed internal oxidative C-H bond activation based on hydroxyl as directing and oxidative group. A range of alkenes and functional groups on acetanilides is supported and a possible mechanism is proposed according to the experimental results.
Oxidative olefination of anilides with unactivated alkenes catalyzed by an (electron-deficient η5-cyclopentadienyl)rhodium(III) complex under ambient conditions
Takahama, Yuji,Shibata, Yu,Tanaka, Ken
supporting information, p. 9053 - 9056 (2015/06/16)
The oxidative olefination of sp2 C-H bonds of anilides with both activated and unactivated alkenes using an (electron-deficient η5-cyclopentadienyl)rhodium(III) complex is reported. In contrast to reactions using this electron-defici
Controlling olefin isomerization in the heck reaction with neopentyl phosphine ligands
Lauer, Matthew G.,Thompson, Mallory K.,Shaughnessy, Kevin H.
, p. 10837 - 10848 (2015/01/08)
The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
Metal-free C-H amination for indole synthesis
Jang, Young Ho,Youn, So Won
supporting information, p. 3720 - 3723 (2014/08/05)
An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
Rh catalyzed olefination and vinylation of unactivated acetanilides
Patureau, Frederic W.,Glorius, Frank
supporting information; experimental part, p. 9982 - 9983 (2010/10/04)
In the catalyzed oxidative olefination of acetanilides (oxidative-Heck coupling), Rh offers great advantages over more common Pd catalysts. Lower catalyst loadings, large functional group tolerance (in particular to halides), and higher reactivity of elec
Pd-catalyzed aerobic oxidative coupling of anilides with olefins through regioselective C-H bond activation
Wang, Jia-Rui,Yang, Chu-Ting,Liu, Lei,Guo, Qing-Xiang
, p. 5449 - 5453 (2008/02/10)
Pd-catalyzed aerobic oxidative coupling of anilides with olefins was achieved through selective C-H bond activation. Compared to the previous studies, not only did we successfully use molecular oxygen to replace the chemical oxidant, but we also obtained
