89523-63-7Relevant articles and documents
Asymmetric Synthesis of Fluorinated Allenes by Rhodium-Catalyzed Enantioselective Alkylation/Defluorination of Propargyl Difluorides with Alkylzincs
Hayashi, Tamio,Ng, Jia Sheng
supporting information, p. 20771 - 20775 (2021/08/25)
The reaction of propargyl difluorides R1CF2C≡CR2 with alkylzincs R3ZnCl giving axially chiral fluorinated allenes R1FC=C=CR2R3 with high enantioselectivity (up to 99 % ee) was found to be catalyzed by a chiral diene/rhodium complex. A key step in the catalytic cycle is selective elimination of one of the enantiotopic fluorides at the β-position of an alkenyl-Rh intermediate, which is generated by regioselective addition of R3-Rh onto the triple bond of the starting difluorides.
TRIAZOLOQUINAZOLINONE SYNTHESIS
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Paragraph 041; 049; 050; 051, (2019/07/13)
The invention relates to an improved process for preparing triazoloquinazolinones of Formula (I), including 9-benzyl-2-(4-methylphenyl)-2,6-dihydro[l,2,4]triazolo[4,3-c]quinazoline-3,5-dione, pharmaceutical compositions comprising the compounds of Formula (I), including 9-benzyl-2-(4- methylphenyl)-2,6-dihydro[l,2,4]triazolo[4,3-c]quinazoline-3,5-dione, prepared by the improved process, and methods of treatment using the compounds of Formula (I), including 9-benzyl-2-(4- methylphenyl)-2,6-dihydro[l,2,4]triazolo[4,3-c]quinazoline-3,5-dione, prepared by the improved process.
Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer
Keaveney, Sinead T.,Kundu, Gourab,Schoenebeck, Franziska
supporting information, p. 12573 - 12577 (2018/09/18)
Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.
Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
Cao, Qun,Howard, Joseph L.,Wheatley, Emilie,Browne, Duncan L.
supporting information, p. 11339 - 11343 (2018/08/28)
A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.
Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes
Woodward, Simon,Ackermann, Miriam,Ahirwar, Saurabh K.,Burroughs, Laurence,Garrett, Mary Robert,Ritchie, John,Shine, Jonathan,Tyril, Bj?rk,Simpson, Kevin,Woodward, Peter
supporting information, p. 7819 - 7824 (2017/06/06)
A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1=Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2=Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2-Ar1CH2(CHO)C=C(CHO)CH2Ar2, which in many cases undergo titanium(IV) chloride-induced double Bradsher closure, providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out.
A practical cobalt-catalyzed cross-coupling of benzylic zinc reagents with aryl and heteroaryl bromides or chlorides
Benischke, Andreas D.,Knoll, Irina,Rérat, Alice,Gosmini, Corinne,Knochel, Paul
supporting information, p. 3171 - 3174 (2016/02/20)
A catalytic system consisting of 5 mol% CoCl2 and 10 mol% isoquinoline allows a convenient cross-coupling of benzylic zinc reagents with various aryl and heteroaryl bromides or chlorides leading to polyfunctionalized diaryl- and aryl-heteroaryl-methane derivatives.
CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides
Fu, Ying,Zhu, Wenbo,Zhao, Xingling,Huegel, Helmut,Wu, Zhouqiang,Su, Yuhu,Du, Zhengyin,Huang, Danfeng,Hu, Yulai
supporting information, p. 4295 - 4299 (2014/06/23)
In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for functionalized sulfone synthesis in the research field of sulfur chemistry. the Partner Organisations 2014.
Nickel-catalyzed C-F bond activation and alkylation of polyfluoroaryl imines
Yang, Xiuxiu,Sun, Hongjian,Zhang, Shumiao,Li, Xiaoyan
, p. 36 - 42 (2013/02/21)
In this paper we show the C-F bond activation and alkylation in polyfluoroaryl imines. An active trimethylphosphine supported nickel-catalyzed cross-coupling reaction of polyfluoroaryl imines with ZnMe2 under mild conditions is described. According to the in situ 19F NMR spectroscopic data, the substrates are quantitatively converted into di-methylation products, while mono-methylation can also be realized under the controlled conditions in moderate yields. Apart from ZnMe2, other organozinc regents were tried in this system. However, due to the nucleophilicity and steric hindrance, they show much lower reactivity than ZnMe2. Only in the case of benzylic zinc chloride, the dibenzylation product can be obtained quantitatively by raising temperature to 90 °C. The results reported here will benefit the development of C-F bond activation as well as the diversity of Schiff bases.
Polyfunctional benzylic zinc chlorides by the direct insertion of magnesium into benzylic chlorides in the presence of LiCl and ZnCl2
Metzger, Albrecht,Piller, Fabian M.,Knochel, Paul
, p. 5824 - 5826 (2009/04/13)
Benzylic zinc chlorides bearing various functional groups are smoothly prepared by the direct insertion of magnesium into benzylic chlorides in the presence of LiCl and ZnCl2. The Royal Society of Chemistry.
