30154-21-3Relevant academic research and scientific papers
Iminyl-Radical-Promoted C-C Bond Cleavage/Heck-Like Coupling via Dual Cobaloxime and Photoredox Catalysis
Tu, Jia-Lin,Tang, Wan,Xu, Wei,Liu, Feng
, p. 2929 - 2940 (2021/02/06)
We report herein an unprecedented protocol for radical-olefin coupling of α-imino-oxy acids and alkenes for the synthesis of alkene-containing nitriles via synergistic photoredox and cobaloxime catalysis. With visible-light irradiation, the transformation
Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism
Weweler, Jens,Younas, Sara L.,Streuff, Jan
, p. 17700 - 17703 (2019/11/13)
A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.
Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters
Zhao, Binlin,Tan, Hui,Chen, Cheng,Jiao, Ning,Shi, Zhuangzhi
, p. 995 - 999 (2018/09/25)
A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano-containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late-stage modification of complex and chiral molecules have also been reported.
Alkenylation of C(sp3)?H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts
Liu, Chuan,Wang, Qiu
supporting information, p. 4727 - 4731 (2018/03/21)
α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C?H zincation and copper-catalyzed C(sp3)?C(sp2) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of β,γ-unsaturated carbonyl compounds.
Synthesis of trans-disubstituted alkenes by cobalt-catalyzed reductive coupling of terminal alkynes with activated alkenes
Mannathan, Subramaniyan,Cheng, Chien-Hong
supporting information, p. 11771 - 11777 (2012/10/30)
A cobalt-catalyzed reductive coupling of terminal alkynes, RC≡CH, with activated alkenes, R'CH=CH2, in the presence of zinc and water to give functionalized trans-disubstituted alkenes, RCH=CHCH2CH 2R', is described. A variety of aromatic terminal alkynes underwent reductive coupling with activated alkenes including enones, acrylates, acrylonitrile, and vinyl sulfones in the presence of a CoCl2/P(OMe) 3/Zn catalyst system to afford 1,2-trans-disubstituted alkenes with high regio- and stereoselectivity. Similarly, aliphatic terminal alkynes also efficiently participated in the coupling reaction with acrylates, enones, and vinyl sulfone, in the presence of the CoCl2/P(OPh)3/Zn system providing a mixture of 1,2-trans- and 1,1-disubstituted functionalized terminal alkene products in high yields. The scope of the reaction was also extended by the coupling of 1,3-enynes and acetylene gas with alkenes. Furthermore, a phosphine-free cobalt-catalyzed reductive coupling of terminal alkynes with enones, affording 1,2-trans-disubstituted alkenes as the major products in a high regioisomeric ratio, is demonstrated. In the reactions, less expensive and air-stable cobalt complexes, a mild reducing agent (Zn) and a simple hydrogen source (water) were used. A possible reaction mechanism involving a cobaltacyclopentene as the key intermediate is proposed. Copyright
A cascade approach to cyclic aminonitrones: reaction discovery, mechanism and scope
Sharma, Rojita,Bulger, Paul G.,McNevin, Michael,Dormer, Peter G.,Ball, Richard G.,Streckfuss, Eric,Cuff, James F.,Yin, Jingjun,Chen, G-Yi
supporting information; experimental part, p. 3194 - 3197 (2009/12/01)
Treatment of ω-epoxynitriles with hydroxylamine affords cyclic aminonitrones in a single step and with high stereoselectivity. The scope of this novel transformation was explored in a series of examples. The aminonitrone products were shown to be useful s
A novel system for the synthesis of nitriles from aldehydes using aqueous ammonia and sodium dichloroiodate
Telvekar, Vikas N.,Patel, Kavit N.,Kundaikar, Harish S.,Chaudhari, Hemchandra K.
, p. 2213 - 2215 (2008/09/18)
A simple and mild method for the conversion of varieties of aldehydes to the corresponding nitriles using aqueous ammonia and aqueous sodium dichloroiodate reagent at room temperature is discussed. Advantages of this system are short reaction time, easy work-up and moderate to good yields.
A novel system for the synthesis of nitriles from carboxylic acids
Telvekar, Vikas N.,Rane, Rajesh A.
, p. 6051 - 6053 (2008/02/10)
A simple, mild and high yielding method for the conversion of various carboxylic acids to nitriles has been developed using diphosphorus tetraiodide in combination with ammonium carbonate at room temperature.
Borrowing hydrogen: Indirect "Wittig" olefination for the formation of C-C bonds from alcohols
Black, Phillip J.,Edwards, Michael G.,Williams, Jonathan M. J.
, p. 4367 - 4378 (2007/10/03)
The successful development of an indirect three-step domino sequence for the formation of C-C bonds from alcohol substrates is described. An iridium-catalysed dehydrogenation of alcohol 1 affords the intermediate aldehyde 2. The desired C-C bond can then be formed by a facile Wittig olefination, yielding the intermediate alkene 3. In the final step the alkene is hydrogenated to afford the indirect Wittig product, the alkane 4. The key to this process is the concept of borrowing hydrogen; hydrogen removed in the initial dehydrogenation step is simply borrowed by the iridium catalyst. Functioning as a hydrogen reservoir, the catalyst facilitates C-C bond formation before subsequently returning the borrowed hydrogen in the final step. Herein we present full details of our examination into both the substrate and reaction scope and the limitations of the catalytic cycle. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Nickel-catalyzed electrochemical couplings of vinyl halides: Synthetic and stereochemical aspects
Cannes,Condon,Durandetti,Perichon,Nedelec
, p. 4575 - 4583 (2007/10/03)
Homo- and cross-coupling involving alkenyl halides have been performed efficiently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, β,γ- or γ,δunsaturated esters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepared with high yields and high stereoselectivity. Partial isomerization is only observed in a few cases, when the alkenyl halide is involved in a late step of the catalytic cycle. This is the case in the preparation of (Z,Z)-1,3-diene.
