Palladium-catalyzed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. Application to the synthesis of substituted nitrogen containing heterocycles

Lepifre, Franck; Clavier, Sylvain; Bouyssou, Pascal; Coudert, G.

doi:10.1016/s0040-4020(01)00651-2

Cited by 62 publications

(15 citation statements)

References 21 publications

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“…tert ‐Butyl 7‐(4‐Methoxyphenyl)‐2,3,4,5‐tetrahydro‐1 H ‐azepine‐1‐carboxylate (3aa): Title compound 3aa was prepared according to the typical procedure using enol phosphate 1a (50 mg, 0.11 mmol). Purification was carried out by flash chromatography (PE/EtOAc: 95:5 to 9:1) to afford 3aa as a white solid (32 mg, 93 %); all data are consistent with the literature 3a…”

Section: Methodssupporting

confidence: 82%

Efficient Cross‐Coupling of Dioxazaborocanes with α‐Phosphate Enamides

et al. 2014

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Section: Methodssupporting

confidence: 82%

Efficient Cross‐Coupling of Dioxazaborocanes with α‐Phosphate Enamides

et al. 2014

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“…Found: C,69.14;H,6.28;N,3.49. 2,3,10,13,14,[2]benzazepin-8-one 14A solution of HCOONH 4 (160 mg, 2.5 mmol) in H 2 O (2 mL) was slowly added to a stirred soln of 13 (0.5 mmol) in MeOH (10 mL) with Pd/C (10%, 10 mg). The mixture was refluxed for 3 h then filtered hot through Celite.…”

Section: 31011-mentioning

confidence: 99%

A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

et al. 2012

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A variety of 3-arylated di-and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.

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“…Previously, Occhiato, Coudert, and Sulikowski have reported isolated examples of cross-couplings of vinyl triflate ( I , Figure 2, top), 7 vinyl phosphate ( II ), 9 and α-iodo enecarbarmate ( III ), 13 respectively, with metalated coupling partners. 7 The instability of I , II , and III , as noted by the authors, 7,13 likely necessitated the use of highly reactive metalated cross-coupling partners.…”

mentioning

confidence: 98%

“…In order to achieve C-2 and/or C-3 functionalization of azepanes, which would provide access to the majority of the substitution patterns resident in the alkaloids shown in Figure 1 , we reasoned that cross-coupling offered the best approach. Previously, Occhiato, Coudert, and Sulikowski have reported isolated examples of cross-couplings of vinyl triflate ( I , Figure 2 , top), 7 vinyl phosphate ( II ), 9 and α-iodo enecarbarmate ( III ), 13 respectively, with metalated coupling partners. 7 The instability of I , II , and III , as noted by the authors, 7 , 13 likely necessitated the use of highly reactive metalated cross-coupling partners.…”

mentioning

confidence: 98%