68036-69-1Relevant articles and documents
Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides
Wang, Chengdong,Guo, Yingjie,Wang, Xiaoming,Wang, Zheng,Ding, Kuiling
supporting information, p. 15903 - 15907 (2021/10/07)
An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,
Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines
Yasukawa, Naoki,Kuwata, Marina,Imai, Takuya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 4409 - 4413 (2018/10/17)
Highly-functionalized pyrroles could be effectively synthesized from 3,6-dihydro-1,2-oxazines using a heterogeneous copper on carbon (Cu/C) under neat heating conditions. Furthermore, the in situ formation of 3,6-dihydro-1,2-oxazines via the hetero Diels-Alder reaction between nitroso dienophiles and 1,3-dienes and the following Cu/C-catalyzed pyrrole synthesis also provided the corresponding pyrrole derivatives in a one-pot manner.
Palladium-Catalyzed Cascade Double C—N Bond Activation: A New Strategy for Aminomethylation of 1,3-Dienes with Aminals
Qiao, Cuifang,Chen, Anrong,Gao, Bingjian,Liu, Yang,Huang, Hanmin
supporting information, p. 929 - 933 (2018/09/22)
A new palladium-catalyzed selective aminomethylation of conjugated 1,3-dienes with aminals via double C—N bond activation is described. This simple method provides an effective and rapid approach for the synthesis of linear α,β-unsaturated allylic amines with perfect regioselectivity. Mechanistic studies disclosed that one palladium catalyst cleaved two distinct C—N bond to furnish a cascade double C—N bond activation, in which an allylic 1,3-diamine and allylic 1,2-diamine were initially formed as key intermediates through the palladium-catalyzed C—N bond activation of aminal and the α,β-unsaturated allylic amine was subsequently produced via palladium-catalyzed C—N bond activation of the allylic diamines.
Zinc(II)-Catalyzed Asymmetric Diels-Alder Reaction of (E)-1-Phenyl Dienes with β,γ-Unsaturated α-Ketoesters
Xiong, Qian,Lin, Lili,Zhao, Xiaohu,Lang, Jiawen,Liu, Xiaohua,Feng, Xiaoming
, p. 12527 - 12534 (2018/10/20)
A highly regio-, diastereo-, and enantioselective Diels-Alder reaction of β,γ-unsaturated α-ketoesters with (E)-1-phenyl dienes has been accomplished by using a stable and easily available chiral N,N′-dioxide/zinc(II) complex as catalyst. Only one isomer of the corresponding cyclohexenes with three chiral centers was obtained in good to excellent yields with excellent ee values under mild reaction conditions. The configurations of the product and chiral N,N′-dioxide/zinc(II) catalyst were identified by X-ray diffraction analysis. In addition, a possible catalytic model was proposed to explain the origin of the asymmetric induction.
Copper-catalyzed radical oxytrifluoromethylation of alkenyl oximes at ambient temperature
Li, Xi-Tao,Lv, Ling,Gu, Qiang-Shuai,Liu, Xin-Yuan
supporting information, p. 6041 - 6046 (2018/09/11)
A mild and efficient copper-catalyzed radical oxytrifluoromethylation reaction of alkenyl oximes was successfully developed. The method provides a straightforward access to a wide range of CF3-containing isoxazolines in good to excellent yields.
Catalyst Controlled Regiodivergent Arylboration of Dienes
Sardini, Stephen R.,Brown, M. Kevin
supporting information, p. 9823 - 9826 (2017/08/02)
A method for the regiodivergent arylboration of dienes is presented. These reactions allow for the formation of a diverse range of synthetically versatile products from simple precursors. Through mechanistic studies, these reactions likely operate by init
A biosynthetically inspired route to substituted furans using the Appel reaction: Total synthesis of the furan fatty acid F5
Lee, Robert J.,Lindley, Martin R.,Pritchard, Gareth J.,Kimber, Marc C.
supporting information, p. 6327 - 6330 (2017/07/11)
Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant. Furthermore, this procedure has been used to deliver an effective total synthesis of the furan fatty acid (FFA) F5.
Synthesis of 1,3-Dienes via a Sequential Suzuki-Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence
Al-Jawaheri, Yassir,Kimber, Marc C.
supporting information, p. 3502 - 3505 (2016/07/23)
We report a facile method for the synthesis of 1,3-dienes by a sequential process consisting of a palladium-catalyzed, base-free, Suzuki-Miyaura coupling/isomerization sequence. This sequence couples boronic acids with propargyl alcohols, generating the requisite allene in situ, followed by conversion of the unactivated allene to its 1,3-diene via a hydro-palladation/dehydro-palladation process. This process is general for a range of boronic acids, including boronic acids with electron-donating and -withdrawing groups, as well as heteroarylboronic acids. Key to this process is the boric acid byproduct of the base-free Suzuki-Miyauru coupling, which generates the required palladium-hydrido complex [H-PdII-OB(OH)2] required for the isomerization.
Direct catalytic cross-coupling of alkenyllithium compounds
Hornillos, Valentn,Giannerini, Massimo,Vila, Carlos,Faans-Mastral, Martn,Feringa, Ben L.
, p. 1394 - 1398 (2015/02/19)
A catalytic method for the direct cross-coupling of alkenyllithium reagents with aryl and alkenyl halides is described. The use of a catalyst comprising Pd2(dba)3/XPhos allows for the stereoselective preparation of a wide variety of substituted alkenes in high yields under mild conditions. In addition (1-ethoxyvinyl)lithium can be efficiently converted into substituted vinyl ethers which, after hydrolysis, give readily access to the corresponding methyl ketones in a one pot procedure.
Ene-diene transmissive cycloaddition reactions with singlet oxygen: The vinylogous gem effect and its use for polyoxyfunctionalization of dienes
Eske, Angelika,Goldfuss, Bernd,Griesbeck, Axel G.,De Kiff, Alan,Kleczka, Margarethe,Leven, Matthias,Neudoerfl, Joerg-M.,Vollmer, Moritz
, p. 1818 - 1829 (2014/03/21)
The singlet oxygen reactivities and regioselectivities of the model compounds 1b-d were compared with those of the geminal (gem) selectivity model ethyl tiglate (1a). The kinetic cis effect is kE/kZ = 5.2 for the tiglate/angelate system 1a/1a′ without a change in the high gem regioselectivity. Further conjugation to vinyl groups enabled mode-selective processes, namely, [4 + 2] cycloadditions versus ene reactions. The site-specific effects of methylation on the mode selectivity and the regioselectivity of the ene reaction were studied for dienes 1e-g. A vinylogous gem effect was observed for the γ,δ-dimethylated and α,γ,δ-trimethylated substrates 1h and 1i, respectively. The corresponding phenylated substrates 1j-l showed similar mode selectivity, as monomethylated 1j exhibited exclusively [4 + 2] reactivity while the tandem products 12 and 14 were isolated from the di- and trimethylated substrates 1k and 1l, respectively. The vinylogous gem effect favors the formation of 1,3-dienes from the substrates, and thus, secondary singlet oxygen addition was observed to give hydroperoxy-1,2-dioxenes 19 and 20 in an ene-diene transmissive cycloaddition sequence. These products were reduced to give alcohols (16, 17, and 18) or furans (24 and 25), respectively, or treated with titanium(IV) alkoxides to give the epoxy alcohols 26 and 27. The vinylogous gem effect is rationalized by DFT calculations showing that biradicals are the low-energy intermediates and that no reaction path bifurcations compete.
