60468-22-6Relevant academic research and scientific papers
Hydrodebromination of allylic and benzylic bromides with water catalyzed by a rhodium porphyrin complex
Yang, Wu,Chen, Chen,Chan, Kin Shing
, p. 12879 - 12883 (2018/10/02)
Hydrodebromination of allylic and benzylic bromides was successfully achieved by a rhodium porphyrin complex catalyst using water as the hydrogen source without a sacrificial reductant. Mechanistic investigations suggest that bromine atom abstraction via a rhodium porphyrin metalloradical operates to give the rhodium porphyrin alkyl species and the subsequent hydrolysis of the rhodium porphyrin alkyl species to a hydrocarbon product is a key step to harness the hydrogen from water.
A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement
Xu, Ming-Hui,Dai, Kun-Long,Tu, Yong-Qiang,Zhang, Xiao-Ming,Zhang, Fu-Min,Wang, Shao-Hua
supporting information, p. 7685 - 7688 (2018/07/15)
A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20?:?1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.
Nickel-Catalyzed Allylic C(sp2)–H Activation: Stereoselective Allyl Isomerization and Regiospecific Allyl Arylation of Allylarenes
Wu, Qiang,Wang, Lanlan,Jin, Rizhe,Kang, Chuanqing,Bian, Zheng,Du, Zhijun,Ma, Xiaoye,Guo, Haiquan,Gao, Lianxun
supporting information, p. 5415 - 5422 (2016/11/22)
Stereoselective allyl isomerization and regiospecific allyl arylation reactions of allylarenes with a catalytic system comprising nickel(II) with an aryl Grignard reagent were studied. Both reactions are triggered by allylic internal C(sp2)–H activation by in-situ-formed Ni0, which is inserted into the C–H bond at the 2-position of the allyl moiety without a directing group. The isomerization of allylarene to 1-propenylarene favors the E isomer and proceeds with quantitative conversion. The arylation takes place through oxidative cross-coupling of allylarenes with excess Grignard reagent. It occurs regiospecifically at the position of C(sp2)–H activation and represents a new method for the synthesis of 1,1-disubstituted olefins. The results of deuterium labeling experiments reveal an alkenyl/alkyl mechanism involving allylic internal C(sp2)–H activation and multiple intermolecular 1,2-, 1,3-, and 2,3-hydride shifts. These methods represent new approaches to the functionalization of olefins, and the mechanistic investigations could be helpful for the discovery and design of new strategies for olefin functionalization.
γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes
Smith, Sean M.,Hoang, Gia L.,Pal, Rhitankar,Khaled, Mohammad O. Bani,Pelter, Liberty S. W.,Zeng, Xiao Cheng,Takacs, James M.
supporting information, p. 12180 - 12182 (2013/01/16)
Directed catalytic asymmetric hydroborations of 1,1-disubstituted alkenes afford γ-dioxaborato amides and esters in high enantiomeric purity (90-95% ee). The Royal Society of Chemistry 2012..
Iridium-catalyzed enantioselective hydrogenation of alkenylboronic esters
Ganic, Adnan,Pfaltz, Andreas
supporting information; experimental part, p. 6724 - 6728 (2012/07/28)
Choose the right ligand: An iridium complex derived from a phosphino-imidazoline ligand is a highly efficient catalyst for the asymmetric hydrogenation of terminal vinyl boronic esters (see scheme). On the other hand, trisubstituted alkenyl-boronates can
One-pot desymmetrizing hydroformylation/carbonyl ene cyclization process: Straightforward access to highly functionalized cyclohexanols
Bigot, Aurelien,Breuninger, Daniel,Breit, Bernhard
supporting information; experimental part, p. 5321 - 5324 (2009/06/06)
(Chemical Equation Presented) Rapid access to highly functionalized alkylidene cyclohexanols through a one-pot desymmetrizing hydroformylation/ carbonyl ene cyclization starting from simple bisalkenylcarbinols is reported. Mechanistic insight into the carbonyl ene reaction is given, highlighting the importance of hyperconjugative substituent effects.
Rh-catalyzed enantioselective hydrogenation of vinyl boronates for the construction of secondary boronic esters
Moran, Wesley J.,Morken, James P.
, p. 2413 - 2415 (2007/10/03)
Rh-catalyzed hydrogenation of prochiral vinyl boronates occurs in an enantioselective fashion in the presence of the chiral ligand Walphos 1. This transformation provides access to chiral secondary organoboronates that are not available from alkene hydrob
Method to inhibit ethylene responses in plants
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Page/Page column 15, (2010/02/11)
The present invention generally relates to methods of inhibiting ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation, by exposing plants to cyclopropene derivatives and compositions thereof wherein: 1) at least one substituent on the cyclopropene ring contains a carbocyclic or heterocyclic ring, or 2) . a substituent contains silicon, sulfur, phosphorous, or boron, or 3) least one substituent contains from one to four non-hydrogen atoms and at least one substituent contains more than four non-hydrogen atoms.
Method of preparing 1,2-dibromo-2-cyano-(substituted)-alkane antimicrobial compounds
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, (2008/06/13)
Method of preparing antimicrobial compounds of the formula: STR1 comprising the following steps: (1) halogenating allyl halide to form 1,2,3-trihalopropane; (2) dehydrohalogenating the 1,2,3-trihalopropane to form 2,3-dihalo-1-propene; (3) treating the 2,3-dihalo-1-propene with a Grignard reagent of the formula R--MgHal, where R is as defined above, followed by treatment with magnesium, to form 3-(R-substituted)-2-magnesiumhalide)-1-propene; (4) treating the 3-(R-substituted)-2-(magnesiumhalide)-1-propene with cyanogen to form 3-(R-substituted)-2-cyano-1-propene; and (5) brominating the 3-(R-substituted)-2-cyano-1-propene to form the desired product.
1,2-Dibromo-2-cyano-2-(aryl)ethane(propane) antimicrobial compounds
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, (2008/06/13)
Antimicrobial compounds of the formulas: STR1 where R1 and R2 are hydrogen; halo; C1-4 alkyl; C1-4 alkoxy; hydroxy; nitro; cyano; or trifluoromethyl; m is 0 or 1; and n is 1 or 2.
