124658-84-0Relevant academic research and scientific papers
A study of (binap)(enyne)tetracarbonyldicobalt(0) complexes
Gibson, Susan E.,Hardick, David J.,Haycock, Peter R.,Kaufmann, Karina A. C.,Miyazaki, Ayako,Tozer, Matthew J.,White, Andrew J. P.
, p. 7099 - 7109 (2007)
Four (binap)(enyne)tetracarbonyldicobalt(0) complexes have been synthesised and their reactivity monitored by variable temperature 31P NMR spectroscopy. Formation of (binap)dicarbonylhydridocobalt(-1) 12 occurred at temperatures between 35 and
Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones
Huang, Jiuzhong,Zheng, Jia,Wu, Wanqing,Li, Jianxiao,Ma, Zhiqiang,Ren, Yanwei,Jiang, Huanfeng
, p. 8191 - 8198 (2017)
The first example of Pd-catalyzed oxidative cyclization of allyltosylamides with acetic acid is reported. This transformation involved C-N/C-C bond formation and provided 3-pyrrolin-2-ones in a one-pot manner with easy-operation, excellent atom economy and good yields. Mechanistic studies indicate that the reaction proceeds through intermolecular aminopalladation, migratory insertion, reinsertion and β-hydride elimination processes.
Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles
Chen, Yang-Bo,Deng, Chao,Liu, Rai-Shung,Liu, Xin,Luo, Chen,Wang, Ze-Shu,Ye, Long-Wu,Zhai, Tong-Yi,Zhang, Yi-Ping
supporting information, p. 17984 - 17990 (2020/08/21)
Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.
Regioselective Wacker-Type Oxidation of Internal Olefins in tBuOH Using Oxygen as the Sole Oxidant and tBuONO as the Organic Redox Cocatalyst
Huang, Qing,Li, Ya-Wei,Ning, Xiao-Shan,Jiang, Guo-Qing,Zhang, Xiao-Wei,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 965 - 969 (2020/02/15)
A regioselective Wacker-Tsuji oxidation of internal olefins in tBuOH has been developed using oxygen as the terminal oxidant and tert-butyl nitrite as the simple organic redox cocatalyst without the involvement of hazardous cocatalysts or harsh reaction conditions. A series of internal olefins bearing various functional groups can be oxidized to the corresponding substituted ketones in generally good yields with high regioselectivities.
Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation
Sun, Qiao,Yoshikai, Naohiko
supporting information, p. 5238 - 5242 (2019/07/08)
A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine de
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
Go, Takashi,Morimatsu, Akane,Wasada, Hiroaki,Tanabe, Genzoh,Muraoka, Osamu,Sawada, Yoshiharu,Yoshimatsu, Mitsuhiro
supporting information, p. 2722 - 2729 (2018/11/21)
A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutyl
Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes
Fu, Shaomin,Chen, Nan-Yu,Liu, Xufang,Shao, Zhihui,Luo, Shu-Ping,Liu, Qiang
, p. 8588 - 8594 (2016/07/27)
Herein, we report a novel cobalt-catalyzed stereodivergent transfer hydrogenation of alkynes to Z- and E-alkenes. Effective selectivity control is achieved based on a rational catalyst design. Moreover, this mild system allows for the transfer hydrogenation of alkynes bearing a wide range of functional groups in good yields using catalyst loadings as low as 0.2 mol %. The general applicability of this procedure is highlighted by the synthesis of more than 50 alkenes with good chemo- and stereoselectivity. A preliminary mechanistic study revealed that E-alkene product was generated via sequential alkyne hydrogenation to give Z-alkene intermediate, followed by a Z to E alkene isomerization process.
A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework
Johnson, Jacob A.,Petersen, Brenna M.,Kormos, Attila,Echeverría, Elena,Chen, Yu-Sheng,Zhang, Jian
supporting information, p. 10293 - 10298 (2016/09/03)
We describe a new strategy to generate non-coordinating anions using zwitterionic metal-organic frameworks (MOFs). By assembly of anionic inorganic secondary building blocks (SBUs) ([In(CO2)4]-) with cationic metalloporphyrin-based organic linkers, we prepared zwitterionic MOFs in which the complete internal charge separation effectively prevents the potential binding of the counteranion to the cationic metal center. We demonstrate the enhanced Lewis acidity of MnIII- and FeIII-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical catalysis.
Synthesis of 3-aza-bicyclo[3.1.0]hexan-2-one derivatives via gold-catalyzed oxidative cyclopropanation of N -allylynamides
Wang, Kai-Bing,Ran, Rui-Qiao,Xiu, Shi-Dong,Li, Chuan-Ying
supporting information, p. 2374 - 2377 (2013/06/27)
N-Allylynamides with various functional groups and different substitution patterns can be converted into 3-aza-bicyclo[3.1.0]hexan-2-one derivatives in moderate to high yield using IMesAuCl/AgBF4 as the catalyst and pyridine N-oxide as the oxidant. A noncarbene mediated approach is proposed as the mechanism.
FeCl3·6H2O and TfOH as catalysts for allylic amination reaction: A comparative study
Trillo, Paz,Baeza, Alejandro,Najera, Carmen
experimental part, p. 2929 - 2934 (2012/06/29)
The use of FeCl3·6H2O and TfOH as readily available and easy-to-handle catalysts for the direct allylic amination reaction using a wide variety of nitrogenated nucleophiles onto different free allylic alcohols is described. Comparative studies between these catalysts, as representative Lewis and Bronsted acids are conducted, concluding that both are suitable catalysts for this transformation. The reactions are performed in a flask open to air and using technical grade 1,4-dioxane. In light of the results obtained from this study it can be asserted that TfOH turned out to be slightly superior than the FeIII salt since similar or better yields are obtained in most of the cases using lower catalyst loadings and milder reaction conditions. A similar trend is observed when carbonucleophiles were employed in the allylic substitution reaction. Studies for the elucidation of the reaction mechanism are in agreement with a carbocationic intermediate, being the regioselectivity governed by the stability of the final product. Copyright
