Pd-catalyzed ortho-olefination of aromatic acetyl esters
- Corresponding author: Song Qiu-Ling, qsong@hqu.edu.cn
Citation:
iang LeiX, Yang Kai, Song Qiu-Ling. Pd-catalyzed ortho-olefination of aromatic acetyl esters[J]. Chinese Chemical Letters,
;2017, 28(3): 517-520.
doi:
10.1016/j.cclet.2016.11.023
Ackermann L., Vicente R., Kapdi A.R.. Transition-metal-catalyzed direct arylation of (hetero) arenes by C-H bond cleavage[J]. Angew. Chem. Int. Ed., 2009,48:9792-9826. doi: 10.1002/anie.v48:52
Chen X., Engle K.M., Wang D.H., Yu J.Q.. Palladium (Ⅱ)-catalyzed C-H activation/C-C cross-coupling reactions:versatility and practicality[J]. Angew. Chem. Int. Ed., 2009,48:5094-5115. doi: 10.1002/anie.v48:28
Lyons T.W., Sanford M.S.. Palladium-catalyzed ligand-directed C-H functionalization reactions[J]. Chem. Rev., 2010,110:1147-1169. doi: 10.1021/cr900184e
Shi W., Liu C., Lei A.. Transition-metal catalyzed oxidative cross-coupling reactions to form C-C bonds involving organometallic reagents as nucleophiles[J]. Chem. Soc. Rev., 2011,40:2761-2776. doi: 10.1039/c0cs00125b
Liu C., Zhang H., Shi W., Lei A.. Bond formations between two nucleophiles:transition metal catalyzed oxidative cross-coupling reactions[J]. Chem. Rev., 2011,111:1780-1824. doi: 10.1021/cr100379j
Engle K.M., Mei T.S., Wasa M., Yu J.Q.. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions[J]. Acc. Chem. Res., 2012,45:788-802. doi: 10.1021/ar200185g
Ding J., Guo Y., Shao L.Y.. Palladium-catalyzed multi-acetoxylation of 1, 3-disubstituted 1H-pyrazole-5-carboxylates via direct C (sp2)-H or C (sp3)-H bond activation[J]. Chin. Chem. Lett., 2016,27:1617-1621. doi: 10.1016/j.cclet.2016.04.007
Lu X., Xiao B., Shang R., Liu L.. Synthesis of unnatural amino acids through palladium-catalyzed C (sp3)-H functionalization[J]. Chin. Chem. Lett., 2016,27:305-311. doi: 10.1016/j.cclet.2015.12.021
Shan G., Huang G.Y., Rao Y., Zhang H.. Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones[J]. Chin. Chem. Lett., 2015,26:1236-1240. doi: 10.1016/j.cclet.2015.07.011
Park S.H., Kim J.Y., Chang S.. Rhodium-catalyzed selective olefination of arene esters via C-H bond activation[J]. Org. Lett., 2011,13:2372-2375. doi: 10.1021/ol200600p
Kim J., Chang S.. Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions[J]. Angew. Chem. Int. Ed., 2014,53:2203-2207. doi: 10.1002/anie.201310544
Graczyk K., Ma W., Ackermann L.. Oxidative alkenylation of aromatic esters by ruthenium-catalyzed twofold C-H bond cleavages[J]. Org. Lett., 2012,14:4110-4113. doi: 10.1021/ol301759v
Shan G., Yang X., Ma L., Rao Y.. Pd-catalyzed C-H oxygenation with TFA/TFAA:expedient access to oxygen-containing heterocycles and late-stage drug modification[J]. Angew. Chem. Int. Ed, 2012,51:13070-13074. doi: 10.1002/anie.201207458
Li G., Wan L., Zhang G.. Pd (Ⅱ)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups[J]. J. Am. Chem. Soc., 2015,137:4391-4397. doi: 10.1021/ja5126897
Hu J., Guan M., Han J.. Palladium-catalyzed ortho-olefination of phenyl acetic and phenyl propylacetic esters via C-H bond activation[J]. J. Org. Chem., 2015,80:7896-7904. doi: 10.1021/acs.joc.5b00775
Gorka Á., Czuczai B., Szoleczky P.. Convenient synthesis of 7, 8-dimethoxytetralin-2-one[J]. Synth. Commun., 2005,35:2371-2378. doi: 10.1080/00397910500187753
Engle K.M., Wang D.H., Yu J.Q.. Ligand-accelerated C-H activation reactions:evidence for a switch of mechanism[J]. J. Am. Chem. Soc., 2010,132:14137-14151. doi: 10.1021/ja105044s
Engle K.M., Thuy-Boun P.S., Dang M., Yu J.Q.. Ligand-accelerated cross-coupling of C (sp2) H bonds with arylboron reagents[J]. J. Am. Chem. Soc., 2011,133:18183-18193. doi: 10.1021/ja203978r
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