85669-63-2Relevant academic research and scientific papers
Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines
Bao, Ming,He, Min,Wang, Yi,Yu, Xiaoqiang
, p. 14720 - 14731 (2021/11/16)
This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).
Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents
Liu, Lihua,Bao, Xifei,Xiao, Hua,Li, Junlan,Ye, Feifan,Wang, Chaoqin,Cai, Qinhua,Fan, Shilu
, p. 423 - 434 (2019/01/08)
A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- A nd stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.
Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation
Horn, Alexander,Kazmaier, Uli
supporting information, p. 4595 - 4599 (2019/06/27)
N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.
Synthesizing method of allyl perfluoroalkyl compound
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, (2019/01/07)
The present invention discloses a synthesizing method of an allyl perfluoroalkyl compound and belongs to the technical field of compound synthesis. Allylphosphonate and a perfluoroalkyl zinc reagent are used to synthesize the allyl perfluoroalkyl compound under a copper catalyst condition. The method is suitable for aromatic hydrocarbon substrates and more suitable for aliphatic substrates, has advantages of mild reaction conditions, simple conditions, good stereoselectivity, etc., and provides an operational method for fluorine-containing blocks needed in life and material sciences.
Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement
Spoehrle, Stéphanie S. M.,West, Thomas H.,Taylor, James E.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 11895 - 11902 (2017/09/07)
A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.
Synthesis of diarylmethanes through palladium-catalyzed coupling of benzylic phosphates with arylsilanes
Zhang, Pengbo,Xu, Jian,Gao, Yuzhen,Li, Xueqin,Tang, Guo,Zhao, Yufen
, p. 2928 - 2932 (2015/01/16)
An efficient approach to the benzylation of arenes has been developed. The reactions described provide straightforward access to diarylmethanes through Pd-catalyzed coupling of benzylic phosphates with arylsilanes in good to excellent yields. The reaction tolerates a wide range of functionalities such as halide, alkoxyl, and nitro groups.
Asymmetric synthesis of α-chiral allylic silanes by enantioconvergent γ-selective copper(I)-catalyzed Allylic Silylation
Delvos, Lukas B.,Vyas, Devendra J.,Oestreich, Martin
supporting information, p. 4650 - 4653 (2013/06/05)
Gamma way: Regio- and enantioselective allylic substitution with a silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation provides direct access to α-chiral allylic silanes from linear acceptors. The enantioconvergent catalysis employing McQuade's six-membered N-heterocyclic-carbene-copper(I) catalyst is applicable to aryl- and alkyl-substituted allylic phosphates (see scheme). Copyright
Short synthesis of chiral 4-substituted (S)-imidazolinium salts bearing sulfonates and their use in γ-selective reactions of allylic halides with grignard reagents
Latham, Christopher M.,Blake, Alexander J.,Lewis, William,Lawrence, Matthew,Woodward, Simon
supporting information; experimental part, p. 699 - 707 (2012/03/11)
A one-pot reaction of Boc-protected amino alcohols and 2-sulfobenzoic anhydride followed by the addition of a wide variety of primary amines has allowed rapid access to diverse libraries of amidosulfonates 1,2-C 6H4(SO3su
Palladium-catalyzed cross-couplings of allylic phosphates
Maslak, Veselin,Tokic-Vujosevic, Zorana,Saicic, Radomir N.
supporting information; experimental part, p. 1858 - 1860 (2009/07/19)
A range of palladium-catalyzed cross-coupling reactions can be performed using allylic phosphates as electrophiles. Both conventional heating and microwave irradiation can be used.
Highly stereoselective cobalt-catalyzed allylation of functionalized diarylzinc reagents
Dunet, Guillaume,Knochel, Paul
, p. 1383 - 1386 (2008/02/13)
Functionalized diarylzinc reagents react readily with allylic chlorides or phosphates in the presence of Co(acac)2 (10 mol%) to give the S N2 products in high yields and with retention of the double-bond configuration. Functionalities like ester, ketone, or cyano are tolerated. Georg Thieme Verlag Stuttgart.
