Copper-catalyzed amination of potassium aryl trifluoroborates using aqueous ammonia

Liesen, André P.; Silva, Arisson T.; Sousa, Jokderléa C.; Menezes, Paulo H.; Oliveira, Roberta A.

doi:10.1016/j.tetlet.2012.06.011

Cited by 14 publications

(9 citation statements)

References 49 publications

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“…These reports include: reviews (Section I), 1149,1150,1151,1152 oxygenation of unactivated benzylic substrates (Section IIA.2), 1153,1154,1155 alkane oxidation (Section II.B), 1156,1157,1158 epoxidation of alkenes (Section II.C.2), 1159 oxidation difunctionalization of alkenes (Section II.C.3), 1160,1161,1162,1163,1164 cross coupling with alkynes (Section II.D.3), 1165 oxidation difunctionalization of alkynes (Section II.D.4), 1166,1167,1168 arene hydroxylation (Section II.E.1), 1169 reactions involving nucleophilic arenes (Section II.E.2), 1170 direction insertion of arenes (Section II.E.3), 1171,1172,1173,1174,1175 functionalization of acidic arene positionos (Section II.E.4), 1176,1177,1178 coupling of carbanion equivalents with boronic acids (Section III.C), 1179,1180,1181,1182,1183,1184,1185 alcohol oxidation (Section IV.A.1),1186,1187,1188,1189,1190,1191,1192,1193,1194,1195,1196,1197,1198,1199 tandem reaction with alcohol oxidation (Section IV.D), 1200,1201,1202,1203,1204,1205,1206,1207,1208 oxidation of aldehydes to amides (Section V.A), 1209 enolate oxiation without cleavage (Section V.C), 1210,1211 oxidative coupling of enolates (Section V.C.1), 1212 α-oxygenation of carboxylic acids (Section V.E), 1213 reaction of hydrazones (Section V.G), 1214 oxidation of hydrazones with cyclization (Section V.G), 12151216 reactions of enamines (Section VI.A), 1217,…”

Section: Discussionmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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Section: Discussionmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…Surprisingly, the synthesis of primary arylamines from arylboronic acids and derivatives has proven to be far more challenging. 8 For example, Fu and co-workers have only recently achieved the cross-coupling of arylboronic acids with aqueous ammonia in the presence of copper(I) oxide (Figure 1, C). 8a …”

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confidence: 99%

Elusive Metal-Free Primary Amination of Arylboronic Acids: Synthetic Studies and Mechanism by Density Functional Theory

et al. 2012

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Herein, we disclose the first metal-free synthesis of primary aromatic amines from arylboronic acids, a reaction that has eluded synthetic chemists for decades. This remarkable transformation affords structurally diverse primary arylamines in good chemical yields, including a variety of halogenated primary anilines that often cannot be prepared via transition metal-catalyzed amination. The reaction is operationally simple, requires only a slight excess of aminating agent, proceeds under neutral or basic conditions and, importantly, it can be scaled up to provide multigram quantities of primary anilines. Density functional calculations reveal that the most likely mechanism involves a facile 1,2-aryl migration and that the presence of an ortho nitro group in the aminating agent plays a critical role in lowering the free energy barrier of the 1,2-aryl migration step.

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“…Olibeira et al have demonstrated a Cu-catalyzed amination of aryltrifluoroborates using aqueous ammonia under mild reaction conditions [100]. This method allows direct access to arylamines and can be carried out in the presence of a variety of functional groups, including aryl bromide, nitrile, nitro, ketone, and aldehyde moieties (Scheme 66).…”

Section: C-n Bond Formationmentioning

confidence: 99%