32507-40-7Relevant academic research and scientific papers
Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis
Guo, Weisi,Wang, Qian,Zhu, Jieping
supporting information, p. 4085 - 4089 (2020/12/25)
Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopy
Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes
Bhowmik, Amit,Fernandes, Rodney A.
supporting information, p. 9203 - 9207 (2019/11/14)
A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.
Palladium-Catalyzed Chemoselective Protodecarboxylation of Polyenoic Acids
Al-Huniti, Mohammed H.,Perez, Mark A.,Garr, Matthew K.,Croatt, Mitchell P.
supporting information, p. 7375 - 7379 (2019/01/03)
Conditions for the first palladium-catalyzed chemoselective protodecarboxylation of polyenoic acids to give the desired polyenes in good yields are presented. The reactions proceed under mild conditions using either a Pd(0) or Pd(II) catalyst and tolerate a variety of aryl and aliphatic substitutions. Unique aspects of the reaction include the requirement of phosphines, water, and a polyene adjacent to the carboxylic acid.
Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes
Yasukawa, Naoki,Yokoyama, Hiroki,Masuda, Masahiro,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 1213 - 1217 (2018/03/28)
Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.
Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
Marcum, Justin S.,Roberts, Courtney C.,Manan, Rajith S.,Cervarich, Tia N.,Meek, Simon J.
supporting information, p. 15580 - 15583 (2017/11/14)
Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.
Synthesis and anti-inflammatory activity of phenylbutenoid dimer analogs
Kim, Sung-Soo,Fang, Yuanying,Park, Haeil
supporting information, p. 1676 - 1680 (2015/07/15)
Several phenylbutenoid dimer (PBD) analogs were synthesized and evaluated for their inhibitory activities against nitric oxide (NO) production and TNF-α release. The PBD analogs were synthesized via Diels - Alder and subsequent Schlosser reactions as key steps. Among the tested compounds, two analogs (8c, 8f) exhibited much stronger inhibitory activity against LPS-stimulated NO production and TNF-α release in RAW 264.7 cells than that of wogonin.
A highly selective synthesis of 1-substituted (E)-buta-1,3-dienes with 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane as building block
Szudkowska-Fratczak, Justyna,Ryba, Aline,Franczyk, Adrian,Walkowiak, Jedrzej,Kubicki, Maciej,Pawluc, Piotr
, p. 137 - 139 (2014/03/21)
Highly selective synthesis of 1-substituted (E)-buta-1,3-dienes via palladium-catalyzed Suzuki-Miyaura cross-coupling of (E)-alkenyl iodides with 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1) is reported. The vinylboronate pinacol ester (1) acts as a vinyl building block to show high chemoselectivity for the Suzuki-Miyaura pathway versus Heck coupling in the presence of biphasic conditions (Pd(PPh3)4, aqueous K 2CO3, toluene and ethanol). Copyright
Titanium-catalyzed intermolecular hydroaminoalkylation of conjugated dienes
Preuss, Till,Saak, Wolfgang,Doye, Sven
, p. 3833 - 3837 (2013/04/24)
Ti me kangaroo down: Conjugated dienes undergo intermolecular hydroaminoalkylation in the presence of Ti catalyst [Ind2TiMe 2] (Ind=η5-indenyl). This new reaction offers a highly atom-efficient approach to homoallylic amines from 1,3-butadienes. Copyright
Stereoselective synthesis of dienes from N-allylhydrazones
Mundal, Devon A.,Lutz, Kelly E.,Thomson, Regan J.
supporting information; experimental part, p. 465 - 468 (2009/07/11)
(Chemical Equation Presented) A new method for the stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives has been developed. High levels of (E)-stereoselectivity are obtained for a variety of substrates. Addition of a dienoph
A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds
Ochiai, Masahito,Ukita, Tatsuzo,Fujita, Eiichi,Tada, Shin-ichi
, p. 1829 - 1839 (2007/10/02)
Organosulfur compounds on treatment with butyllithium in tetrahydrofuran followed by tributylstannylmethyl iodide 1 afforded olefins.The reaction was found to proceed via the destannylsulfurization of the initially formed β-stannyl organosulfur compounds.Thus, allyl 2-pyridyl sulfides 2 or allyl phenyl sulfones 12 were converted into 1,3-dienes 4.Compounds 13 and 15 were converted into the olefins 14 and 17.Furthermore, the reaction was applied to the synthesis of α-substituted vinyl sulfides 24 and allene 27.The stereochemistry of the double bond is discussed.Keywords - destannylsulfurization; allyl 2-pyridyl sulfide; allyl phenyl sulfone; synthesis of olefin; 1,3-diene; vinyl sulfide; β-tributylstannyl organosulfur compound.
