72331-10-3Relevant articles and documents
Synthesis of Aromatic Esters, Lactones, Anhydrides, and Heterocycles via Thallation-Carbonylation of Arenes
Larock, Richard C.,Fellows, Constance A.
, p. 363 - 365 (1980)
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.
Nickel-Catalyzed Stereospecific C?H Coupling of Benzamides with Epoxides
Xu, Shibo,Takamatsu, Kazutaka,Hirano, Koji,Miura, Masahiro
supporting information, p. 11797 - 11801 (2018/09/10)
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.
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.
