26642-57-9Relevant academic research and scientific papers
Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes
Zhang, Kena,Provot, Olivier,Alami, Mouad,Tran, Christine,Hamze, Abdallah
, p. 1249 - 1261 (2022/02/07)
This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis
Binary-Acid Catalysis with Sc(OTf)3/TfOH in the Alkenylation of Arenes with Alkynes
Zhang, Wenxuan,Sun, Jiaying,Xiang, Linrui,Si, Wen,Song, Ran,Yang, Daoshan,Lv, Jian
, p. 5998 - 6003 (2021/07/31)
Herein we report binary acid Sc(OTf)3/TfOH-catalyzed alkenylation of arenes with alkynes. In this system, the high-energy vinyl carbocations with activated and weakly coordinating trifluoromethanesulfonate anions by Lewis acid Sc(III) can undergo facile F
Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis
Babu, Reshma,Balaraman, Ekambaram,Midya, Siba P.,Subaramanian, Murugan,Yadav, Vinita
, p. 7552 - 7562 (2021/06/28)
The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.
Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions
Jereb, Marjan,Vra?i?, Dejan
, p. 747 - 762 (2018/01/17)
Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.
Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α-Chloroalkenyl Boronates
Zeng, Yao-Fu,Ji, Wei-Wei,Lv, Wen-Xin,Chen, Yunyun,Tan, Dong-Hang,Li, Qingjiang,Wang, Honggen
, p. 14707 - 14711 (2017/10/23)
The individual molecules of α-chloroalkenyl boronates include both an electrophilic C?Cl bond and a nucleophilic C?B bond, which makes them intriguing organic synthons. Reported herein is a stereodivergent synthesis of both E and Z α-chloroalkenyl N-methyliminodiacetyl (MIDA) boronates through the direct chlorination of alkenyl MIDA boronates using tBuOCl and PhSeCl reagents, respectively. Both reaction processes are stereospecific and the use of sp3-B MIDA boronate is the key contributor to the reactivity. The synthetic value of the boronate products was also demonstrated.
Effective palladium-catalyzed synthesis of triarylethene-based molecules in aqueous solution
Zhu, Yan,Sun, Peng,Yang, Hailong,Lu, Linhua,Yan, Hong,Creus, Marc,Mao, Jincheng
experimental part, p. 4831 - 4837 (2012/09/22)
Highly effective and selective Pd-catalyzed coupling reactions of 1,1-dibromo-1-alkenes with various arylboronic acids have been performed in aqueous solution under mild conditions. The method is simple, economic, and practical for the synthesis of triarylethene-based compounds. Copyright
A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite
Wang, Tongqiang,Hu, Yuanyuan,Zhang, Songlin
supporting information; experimental part, p. 2312 - 2315 (2010/07/09)
The widely available carbonyl compounds react with Grignard reagents in the presence of diethyl phosphite to give the corresponding olefins in good to excellent yields: A range of conjugated dienes, terminal olefins, multisubstituted-alkenes and conjugated enynes could be readily obtained by the method in mild conditions.
Aminophosphine palladium pincer complexes for Suzuki and Heck reactions
Bolliger, Jeanne L.,Frech, Christian M.
scheme or table, p. 23 - 28 (2010/04/24)
The aminophosphine-based pincer complexes [C6H 3-2,6-{NHP(piperidinyl)2}2Pd(CI)] (2) and [C6H3-2,6-{OP(piperidinyl)2}2Pd(CI)] (3) are readily prepared from cheap starting materials by sequential addition of 1,1′,1 "-phosphinetriyltripiperidine and 1,3-diaminobenzene or resorcinol to solutions of [Pd(cod)(CI)2] (cod = cyclooctadiene) in toluene under N2 in 'one pot'. Compounds 2 and 3 proved to be not only excellent catalysts for the Suzuki and the Heck cross-coupling reactions, but they are also very convenient to use: The toluene solutions of the 'one-pot' syntheses can be used directly for the catalytic reactions, thereby saving the time-consuming isolation of the catalysts. The Suzuki cross-coupling reaction catalyzed by 2 and 3 can be performed in air at 100 °C in toluene of technical quality: in the presence of only 0.001 mol% of catalyst, several electronically deactivated and sterically hindered aryl bromides are quantitatively coupled with phenylboronic acid within a few minutes of reaction time. Furthermore, complex 2 enables the use of activated and non-activated aryl chlorides as coupling partners in the Suzuki reaction. Compounds 2 and 3 have also been shown to be highly active and reliable Heck catalysts: Very low catalyst loadings and short reaction times are required for the quantitative coupling of several electronically deactivated and sterically hindered aryl bromides with various olefins at 140 °C. At increased temperatures, even electronically deactivated and sterically hindered aryl chlorides can be efficiently coupled with olefins in the presence of only 0.01 mol% of catalyst. Schweizerische Chemische Gesellschaft.
Palladium-catalysed direct synthesis of benzo[b]thiophenes from thioenols
Inamoto, Kiyofumi,Arai, Yukari,Hiroya, Kou,Doi, Takayuki
supporting information; experimental part, p. 5529 - 5531 (2009/04/13)
The one-pot conversion of thioenols into benzo[b]thiophenes was achieved by using a simple palladium catalyst such as PdCl2 or PdCl 2(cod). The Royal Society of Chemistry.
Palladium-catalyzed hydroarylation of alkynes with arenediazonium salts
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Persiani, Daniela
scheme or table, p. 1597 - 1600 (2009/04/10)
The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (2)-2-arylcinnamates stereo- and regioselectively.
