- Synthesis of 3-Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)-Catalyzed C–H Activation
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A straightforward and convenient route has been developed for the synthesis of 3-unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)-catalyzed C–H activation. The reaction proceeds through tandem ortho-hydroxymethylation of aryl amide and subsequent intramolecular lactonization.
- Zhou, Chao,Zhao, Junqi,Chen, Wenkun,Imerhasan, Mukhtar,Wang, Jun
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supporting information
p. 6485 - 6488
(2020/10/02)
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- Heterogeneous One-Pot Carbonylation and Mizoroki–Heck Reaction in a Parallel Manner Following the Cleavage of Cinnamaldehyde Derivatives
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Carbon monoxide (CO) and styrene derivatives that can be both generated by a palladium on carbon (Pd/C)-catalyzed carbon–carbon (C?C) bond cleavage reaction of cinnamaldehyde derivatives were effectively utilized in further palladium-catalyzed C?C bond forming reactions in a direct and practical way. CO derived from simple and affordable CO carriers such as cinnamaldehyde or terephthalaldehyde was efficiently employed in the in situ CO fixation with various aromatic iodides through a palladium-catalyzed carbonylation followed by an inter- or intramolecular coupling reaction with alcohols to afford the corresponding esters or lactones, respectively. Styrene derivatives were also efficient substrates in an in situ Mizoroki–Heck-type cross-coupling reaction with aryl iodides, leading to the effective formation of asymmetric stilbenes. The decarbonylation of cinnamaldehyde derivatives and the subsequent independent syntheses of both esters/lactones and 1,2-diarylethenes could be achieved in a virtual one-pot and in situ reaction using a H-shaped pressure-tight glass-sealed tube consisting of two independent but laterally connected reaction tubes in the gas space.
- Hattori, Tomohiro,Ueda, Shun,Takakura, Ryoya,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
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p. 8196 - 8202
(2017/06/23)
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- SYNTHESIS OF (Z)-3-BUTYLIDENE-6,7-DIHYDROXYPHTHALIDE
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(Z)-3-Butylidene-6,7-dihydroxyphthalide (2) was first synthesized from 6,7-dimethoxyphthalide (4) and its structure was synthetically confirmed.
- Ogawa, Yoshimitsu,Hosaka, Kunio,Chin, Masao,Mitsuhashi, Hiroshi
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p. 1737 - 1744
(2007/10/02)
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- Naturally Occuring Dibenzofurans. Part 9. A Convenient Synthesis of Phthalides: The Synthesis of Methyl Di-O-methylporphyrilate
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A convenient synthesis of phthalides from o-halogenobenzyl alcohols is described.This method is then applied to the synthesis of methyl di-O-methylporphyrilate (methyl 1,3-dihydro-4,10-dimethoxy-8-methyl-3-oxoisobenzofuro
- Sargent, Melvyn V.
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p. 231 - 236
(2007/10/02)
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- COBALT-CATALYSED CARBONYLATION OF ARYL HALIDES
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A novel method for carbonylation of aromatic and heteroatomatic halides is described.The catalytic system consists of a combination of alkylcobalt carbonyl complexes, either performed or made "in situ", and bases such as alkoxides, NaOH and K2CO3 in aliphatic alcohols.Under these conditions new anionic cobalt complexes are formed which are characterized by a very high reactivity towards aromatic halides.The latter undergo the carbonylation reaction with high yield under very mild conditions.
- Foa, M.,Francalanci, F.,Bencini, E.,Gardano, A.
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p. 293 - 304
(2007/10/02)
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- SYNTHESIS OF ISOINDOLOISOQUINOLINE ALKALOIDS. A REVISION OF THE STRUCTURE OF (+/-)-NUEVAMINE
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An easy and efficient method for the synthesis isoindoloisoquinolines, and the assignment of a new structure for the alkaloid (+/-)-nuevamine are reported.
- Alonso, Ricardo,Castedo, Luis,Dominguez, Domingo
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p. 2925 - 2928
(2007/10/02)
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- Synthesis of Aromatic Carbonyl Compounds via Thallation-Carbonylation of Arenes
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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.
- Larock, Richard C.,Fellows, Constance A.
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p. 1900 - 1907
(2007/10/02)
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