6538-16-5Relevant articles and documents
Nickel-Catalyzed Stereospecific C?H Coupling of Benzamides with Epoxides
Xu, Shibo,Takamatsu, Kazutaka,Hirano, Koji,Miura, Masahiro
, p. 11797 - 11801 (2018)
A Ni(OAc)2-catalyzed C?H coupling of 8-aminoquinoline-derived benzamides with epoxides has been developed. The reaction proceeds with concomitant removal of the 8-aminoquinoline auxiliary to form the corresponding 3,4-dihydroisocoumarins directly. Additionally, the nickel catalysis is stereospecific, and the cis- and trans-epoxides are converted into the corresponding cis- and trans-dihydroisocoumarins with retention of configuration, which is complementary to previously reported palladium catalysis. Moreover, while still preliminary, the Csp3?H functionalization is also achieved in the presence of modified NiCl2 catalysts.
Palladium/Acid Relay Catalyzed Tandem Heck Coupling/6-Endo Cyclization between ortho-Halogenated Benzoates and Unactivated Terminal Alkenes for the Synthesis of 1-Isochromanones
Wen, Zhen-Kang,Ge, Xiao-Min,Zhao, Ze-Kai,Chao, Jian-Bin
supporting information, p. 983 - 988 (2019/01/30)
We report a unique and expeditious route to synthesize 1-isochromanone derivatives through palladium catalyzed tandem Heck coupling/6-endo hydroacyloxylation cyclization between readily available ortho-halogenated benzoates and unactivated alkenes. Various 2-bromo or 2-iodo benzoates can be coupled efficiently with a broad range of alkenes to afford functionalized 1-isochromanones in high yields. Significantly, this cost-efficient and easy-to-handle synthetic methodology will have great prospect application in the synthetic and medicinal chemistry. (Figure presented.).
SYNTHESIS OF ISOCOUMARINS VIA THALLATION-OLEFINATION OF BENZOIC ACIDS
Larock, R. C.,Varaprath, S.,Lau, H. H.,Fellows, C. A.
, p. 5274 - 5284 (2007/10/02)
Benzoic acid and substituted benzoic acids are readily thallated by thallium(III) trifluoroacetate and subsequently reacted with palladium chloride and simple olefins, allylic halides, vinyl halides, or vinyl esters to give isocoumarins.The organic halide reactions are catalytic in palladium. 1,2- and 1,3-dienes also react catalytically to afford 4-alkylidene- and 3-vinyl-3,4-dihydroisocoumarins, respectively.Vinylcyclopropanes also afford 3-vinyl-3,4-dihydroisocoumarins.This highly convenient thallation-olefination approach appears quite general for the synthesis of isocoumarins.
Synthesis of Aromatic Carbonyl Compounds via Thallation-Carbonylation of Arenes
Larock, Richard C.,Fellows, Constance A.
, p. 1900 - 1907 (2007/10/02)
Simple arenes, substituted benzylic and β-phenylethyl alcohols, benzoic acid, phenylacetic acid, benzamide, acetanilide, phenylurea, and benzophenone have been thallated under variety of reaction conditions with thallium(III) trifluoroacetate and subsequently carbonylated with 19percent PdCl2, 2 equiv of LiCl, and MgO in either methanol or tetrahydrofuran under 1 atm of carbon monoxide to give aromatic esters, substituted phthalides and 3,4-dihydroisocoumarins, phthalic and homophthalic anhydride, phthalimide, and the ortho-substituted methyl esters of acetanilide, phenylurea, and benzophenone, respectively.The scope and limitations of this approach to aromatic carbonyl compounds are examined.
Synthesis of Aromatic Esters, Lactones, Anhydrides, and Heterocycles via Thallation-Carbonylation of Arenes
Larock, Richard C.,Fellows, Constance A.
, p. 363 - 365 (2007/10/02)
The thallation and subsequent palladium-catalyzed carbonylation of simple arenes, benzylic and β-phenethyl alcohols, benzoic and phenylacetic acids, benzamide, and acetanilide afford benzoate esters, phthalides, 3,4-dihydroisocoumarins, phthalic and homophthalic anhydrides, phthalimide, and acetylanthranil, respectively.The carbonylation reaction proceeds in excellent yield at room temperature and atmospheric pressure and is highly stereo- and regioselective.
