87143-30-4Relevant academic research and scientific papers
Synthesis of Spiro-dihydroquinoline and Octahydrophenanthrene Derivatives via Palladium-Catalyzed Intramolecular Oxidative Arylation
Zang, Zhong-Lin,Karnakanti, Shuklachary,Zhao, Sheng,Hu, Ping,Wang, Zhen,Shao, Pan-Lin,He, Yun
supporting information, p. 1354 - 1357 (2017/03/23)
A method for intramolecular sp2 C-H oxidative arylation of unactivated cyclic olefins has been developed to access spiro-dihydroquinoline and octahydrophenanthrene derivatives in a straightforward and efficient manner. Bearing picolinamide as a directing group, the alkenyl anilines cyclized to afford spiro-dihydroquinolines in moderate to excellent yields via direct oxidative arylation, while the alkenyl benzylamines furnished the octahydrophenanthrene derivatives in moderate yields via sequential oxidative arylation and double acetoxylation.
Catalytic Multisite-Selective Acetoxylation Reactions at sp2 vs sp3 C-H Bonds in Cyclic Olefins
Zang, Zhong-Lin,Zhao, Sheng,Karnakanti, Shuklachary,Liu, Cheng-Lin,Shao, Pan-Lin,He, Yun
supporting information, p. 5014 - 5017 (2016/10/14)
The first Pd-catalyzed multisite-selective acetoxylation reactions are disclosed at an unactivated alkene sp2 C-H bond versus secondary allylic sp3 C-H bond in cyclic olefins via the modulation of directing groups. The different directing groups overcome the key challenge in differentiating C-H bonds and provide a new controlling approach for site-specific C-H activation. A wide variety of substrates are readily acetoxylated under operationally simple conditions. Mechanistic studies suggest that different Pd (IV) intermediates were involved in the multisite-selective acetoxylation reactions.
Efficient hydrolysis of nitriles to amides with hydroperoxide anion in aqueous surfactant solutions as reaction medium
Brinchi, Lucia,Chiavini, Lisa,Goracci, Laura,Di Profio, Pietro,Germani, Raimondo
experimental part, p. 175 - 179 (2010/04/23)
Aliphatic and aromatic nitriles are converted to corresponding amides in a single step via hydrolysis with basic H2O2 in aqueous solution of the surfactant Cetyltrimethylammonium methanesulfonate (CTAOMs). The method has several advantages: use and recycle of water as reaction medium, use of environmentally benign oxidant H2O2, easy product isolation, short reaction time, high yields and selectivity, mild conditions.
Acyl and Sulfonyl Isocyanates ib β-Lactam Synthesis
Barrett, Anthony G. M.,Betts, Michael J.,Fenwick, Ashley
, p. 169 - 175 (2007/10/02)
The preparation of β-lactams from the reactions of several acyl and sulfonyl activated isocyanates with alkenes was studied.Three compounds, (2,2,2-trichloroethoxy)sulfonyl, 2,2,2-trichloroethane sulfonyl, and trifluoroacetyl isocyanates, were shown to be
2,2,2-Trichloroethylsulphonyl, 2,2,2-Trichloroethoxysulphonyl, and Trifluoroacetyl Isocyanates in β-Lactam Synthesis
Barrett, Anthony G. M.,Fenwick, Ashley,Betts, Michael J.
, p. 299 - 301 (2007/10/02)
Condensation of the title isocyanates with olefins and subsequent dissolving-metal reduction (sulphonyl derivates) or chromatography on Florisil (trifluoroacetyl derivatives) gave several N-unsubstituted β-lactams including two 8-aza-2-oxabicyclooc
Mechanism of the Reaction of Nitriles with Alkaline Hydrogen Peroxide. Reactivity of Peroxycarboximidic Acid and Application to Superoxide Ion Reaction
Sawaki, Yasuhiko,Ogata, Yoshiro
, p. 793 - 799 (2007/10/02)
Formation of peroxycarboximidic acid (1) is not rate-determining in the reaction of nitrile with alkaline hydrogen peroxide to form amide and oxygen; the yield of amide based on H2O2 varies from 20 to 60percent.When dimethyl sulfoxide (DMSO), a reactive substrate, is added, the rate is independent of and governed in turn by a rate-determining addition of HOO- to nitrile.This reaction gives a reliable α-value of kHOO-/kHO-, which is 10000 for benzonitrile.A facile conversion of nitrile to amide may be achieved by the reaction in the presence of DMSO, unacco mpanied by side reactions such as the epoxyamide formation from α,β-unsaturated nitrile.Kinetics and product analysis suggest that a predominant reaction is not a non-radical oxidation of H2O2 with 1 but a radical decomposition of H2O2 which is induced by the homolysis of anion of 1 (1A).No singlet oxygen could be trapped chemically.The reaction of superoxide ion, O2-., with acetonitrile is shown to be analogous to that of HOO-; the decomposition of O2-. is fast in the presence of MeCN and DMSO in benzene, affording acetamide and dimethyl sulfone.
