2021
DOI: 10.1002/chem.202102734
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Facile Synthesis of Alkylidene Phthalides by Rhodium‐Catalyzed Domino C−H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids

Abstract: The Rh-catalyzed ortho-C(sp 2 )À H functionalization of 8-aminoquinoline-derived benzamides with aliphatic acyl fluorides generated in situ from the corresponding acids has been developed. This reaction initiated with 8-aminoquinoline-directed ortho-C(sp 2 )À H acylation, which was accompanied by subsequent intramolecular nucleophilic acyl substitution of amide group to produce alkylidene phthalides This approach exhibits high stereo-selectivity for Z-isomer products, and tolerates a variety of functional grou… Show more

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Cited by 2 publications
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“…More recently, Su and Shang developed a rhodium‐catalyzed protocol for cascade C−H acylation/intramolecular nucleophilic acyl substitution of benzamides with a large range of available carboxylic acids using 8‐aminoquinoline as directing group (Scheme 33). [40] Aliphatic acyl fluorides were generated in situ from the corresponding acids using fluoro‐dipyrrolidinocarbenium‐hexafluorophosphate (BTFFH) as fluorinating reagent.…”
Section: C‐h Cross Couplingmentioning
confidence: 99%
“…More recently, Su and Shang developed a rhodium‐catalyzed protocol for cascade C−H acylation/intramolecular nucleophilic acyl substitution of benzamides with a large range of available carboxylic acids using 8‐aminoquinoline as directing group (Scheme 33). [40] Aliphatic acyl fluorides were generated in situ from the corresponding acids using fluoro‐dipyrrolidinocarbenium‐hexafluorophosphate (BTFFH) as fluorinating reagent.…”
Section: C‐h Cross Couplingmentioning
confidence: 99%