113947-89-0Relevant academic research and scientific papers
Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction
Xu, Wen-Lei,Tang, Lei,Ge, Chen-Yu,Chen, Jie,Zhou, Ling
supporting information, p. 2268 - 2273 (2019/04/10)
A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).
Metal-Free Dehydrogenative Diels-Alder Reactions of Prenyl Derivatives with Dienophiles via a Thermal Reversible Process
Xu, Wen-Lei,Zhang, Heng,Hu, Yu-Long,Yang, Hui,Chen, Jie,Zhou, Ling
supporting information, p. 5774 - 5778 (2018/09/21)
An efficient dehydrogenative Diels-Alder reaction of prenyl derivatives with dienophiles has been developed. The reaction exhibits broad substrate scope and provides efficient access to cyclohexene derivatives with good to excellent yields. A reasonable mechanism involving a metal-free thermal reversible process is proposed.
Palladium-catalyzed completely linear-selective negishi cross-coupling of allylzinc halides with aryl and vinyl electrophiles
Yang, Yang,Mustard, Thomas J. L.,Cheong, Paul Ha-Yeon,Buchwald, Stephen L.
supporting information, p. 14098 - 14102 (2014/01/06)
Completely linear: The title reaction provides an effective means to access a wide range of prenylated arenes and skipped dienes in a completely linear-selective fashion, as demonstrated by a concise synthesis of the anti-HIV natural product siamenol. DFT calculations shed light on the origin of the excellent regioselectivity observed with the current Pd-based catalyst system. Copyright
Ligand-controlled palladium-catalyzed regiodivergent suzuki-miyaura cross-coupling of allylboronates and aryl halides
Yang, Yang,Buchwald, Stephen L.
, p. 10642 - 10645 (2013/08/23)
An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the
Arylcyclopropane Photochemistry. Substituent Effects on the Photochemical 1,3-Hydrogen Migration of 1,1-Dimethyl-2-phenylcyclopropane
Hixson, Stephen S.,Gallucci, Charles R.
, p. 2711 - 2713 (2007/10/02)
Irradiation of 1,1-dimethyl-2-arylcyclopropanes 1a-g (Ar = p-CF3C6H4 (1a), m-CF3C6H4 (1b), p-CH3C6H4 (1c), m-CH3C6H4 (1d), C6H5 (1e), m-OCH3C6H4 (1f), p-OCH3C6H4 (1g) gave in every case a 2-methyl-4-aryl-1-butene (2a-g) via a 1,3-hydrogen migration, accompanied by lesser amounts of a 3-methyl-1-aryl-2-butene (3a-g).Rearrangement is a singlet-state process.Rate constants for rearrangement were determined from reactant fluorescence lifetimes and product quantum yields.The rates for rearrangament of 1 to 2 were as follows:1a, 25*106s-1; 1b,15*106s-1; 1c, 7.9*106s-1; 1d, 6.1*106s-1; 1e, 2.3*106s-1; 1f, 1.9*106s-1; 1g, 0.87*106s-1.It isconcluded that the energetics of cyclopropane ring opening are important in the rate-determining step of the reaction.
