2011
DOI: 10.1021/ol202609a
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Palladium-Catalyzed Decarboxylative Coupling of Isatoic Anhydrides with Arylboronic Acids

Abstract: The decarboxylative coupling of isatoic anhydrides with arylboronic acids was realized for the first time in the presence of Pd(2)(dba)(3) and DPEphos, achieving aryl o-aminobenzoates with yields ranging from moderate to good. The efficiency of this procedure was demonstrated by good compatibility with fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, formacyl, acetyl, thienyl, and naphthyl groups. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dio… Show more

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Cited by 35 publications
(9 citation statements)
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“…HRMS (ESI) m / z [M + H] + calcd for C 13 H 11 N 2 O 4 259.0719, found 259.0709. The characterization data is consistent with reported literature …”
Section: Methodssupporting
confidence: 91%
See 1 more Smart Citation
“…HRMS (ESI) m / z [M + H] + calcd for C 13 H 11 N 2 O 4 259.0719, found 259.0709. The characterization data is consistent with reported literature …”
Section: Methodssupporting
confidence: 91%
“…[M + H] + calcd for C 14 H 11 N 2 O 2 239.0821, found 239.0820. The characterization data is consistent with reported literature 32. 4-Acetylphenyl 2-Aminobenzoate (7e).…”
supporting
confidence: 91%
“…On the basis of our previous studies on aerobic oxidative coupling reactions,6,9b we postulated that readily available arylboronic acids could be used as coupling partners with acyl chlorides via aerobic oxidative coupling by employing an appropriate oxidant. As suggested by our previous work,9b we began our investigation by testing the reaction of benzoyl chloride ( 1a ) with phenylboronic aicd ( 2a ) using bis[(2‐diphenylphosphino)phenyl] ether (DPEphos) as ligand, 1‐methylpiperine as base, and O 2 as oxidant in the presence of catalytic amounts of palladium catalysts in dry THF. To our delight, a trace amount of the desired phenyl benzoate ( 3aa ) was detected by GC‐MS.…”
Section: Methodsmentioning
confidence: 99%
“…To the best of our knowledge, the synthesis of diarylmethanols using aryltriolborates as coupling partners has very few reports to date [ 32 ], even though aryltriolborates have exceptionally high levels of stability in air/water, reasonable solubility in organic solvents, and are generally used as the aryl source for C-C and C-N bond-forming reactions [ 38 , 39 , 40 , 41 , 42 , 43 ]. As part of the continuing efforts in our laboratory toward the development of palladium-catalyzed addition reactions [ 33 , 34 , 35 , 36 , 37 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ], we herein report a simple and efficient protocol for the synthesis of diarylmethanols by the Pd-catalyzed base-free addition of aryltriolborates to aldehydes ( Scheme 1 ).…”
Section: Introductionmentioning
confidence: 99%