A simple and mild TEMPO-CuCl catalyzed aerobic oxidation of primary and secondary alcohols in ionic liquid [bmim][PF6] gave the corresponding aldehydes and ketones with no trace of overoxidation to carboxylic acids. The product can be isolated by a simple extraction with organic solvent, and the ionic liquid can be recycled or reused.
I. A. Ansari, R. Gree, Org. Lett., 2002, 4, 1507-1509.
A four-component system consisting of acetamido-TEMPO/Cu(ClO4)2/TMDP/DABCO in DMSO allows an efficient room-temperature aerobic alcohol oxidation of various alcohols into their corresponding aldehydes or ketones in good to excellent yields. The catalytic system can be recycled.
N. Jiang, A. J. Ragauskas, J. Org. Chem., 2006, 71, 7087-7090.
The system Cu(ClO4)2/acetamido-TEMPO/DMAP catalyses the room-temperature aerobic oxidation of primary alcohols to aldehydes in the ionic liquid [bmpy]PF6. The catalysts can be recycled and reused.
N. Jiang, A. J. Ragauskas, Org. Lett., 2005, 7, 3689-3692.
Ubiquitous carboxylic acids can serve as starting materials for a photocatalytic decarboxylative C-O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products.
S. Senaweera, K. C. Cartwrigt, J. A. Tunge, J. Org. Chem., 2019, 84, 12334-12343.
A direct metal-free α-hydroxylation of α-unsubstituted β-oxoesters and β-oxoamides using m-chloroperbenzoic acid as the oxidant enables straightforward metal-free access to important α-hydroxy-β-dicarbonyl moieties under mild reaction conditions. Furthermore, the hydroxylated products can readily be converted into vicinal tricarbonyl compounds, which are useful synthetic precursors.
H. Asahara, N. Nishiwaki, J. Org. Chem., 2014, 79, 11735-11739.
A facile nickel-catalyzed oxidation of primary alcohols with tetrabutylammonium peroxydisulfate in the presence of ammonium hydrogen carbonate under basic aqueous conditions provides access to various aliphatic, aromatic and heterocyclic nitriles in excellent yields with very high purity.
F.-E. Chen, Y.-Y. Li, M. Xu, H.-Q. Jia, Synthesis, 2002, 1804-1806.
A general Pd-catalyzed oxidative aminocarbonylation of arylsilanes under mild conditions is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines.
J. Zhang, Y. Hou, Y. Ma, M. Szostak, J. Org. Chem., 2019, 84, 120-127.
An enantioselective alkoxycarbonylation-amination cascade process of terminal allenes with CO, methanol, and arylamines proceeds under mild conditions (r.t., ambient pressure CO) via oxidative Pd(II) catalysis using a chiral aromatic spiroketal-based diphosphine ligand and a Cu(II) salt as an oxidant to afford various α-methylene-β-arylamino acid esters in good yields with excellent enantioselectivity and high regioselectivity.
J. Liu, Z. Han, X. Wang, Z. Wang, K. Ding, J. Am. Chem. Soc., 2015, 137, 15346-15349.
Ethyl bromodifluoroacetate as carbonyl source enables an efficient direct carbonation of aromatic acids to yield monoalkyl phthalate derivatives in good yields. A broad range of substrates bearing various functional groups were tolerated.
N. Tao, J. Wang, C. Yuan, R. Zeng, Y.-S. Zhao, Org. Lett., 2019, 21, 8607-8610.
A Pd(II)-catalyzed oxidative approach to construct polysubstituted pyrroles from N-homoallylicamines and arylboronic acids proceeds through cascade formation of C-C and C-N bonds via oxidative arylation of unactive alkenes, followed by intramolecular aza-Wacker cyclization.
J. Zheng, L. Huang, C. Huang, W. Wu, H. Jiang, J. Org. Chem., 2015, 80, 1235-1242.
A Cu(OAc)2-promoted oxidation/[3+2]cycloaddition/aromatization cascade reaction provides tetrasubstituted NH-pyrroles in very good yields from a wide range of chalcones and diethyl iminodiacetates. This convenient methodology has several advantages, such as the use of easily accessible chalcones and readily available diethyl iminodiacetates, and mild reaction conditions.
Z.-q. Lin, C.-d. Li, Z.-c. Zhou, S. Xue, J.-r. Gao, Q. Ye, Y.-j. Li, Synlett, 2019, 30, 1442-1446.
A novel palladium-catalyzed oxidative, intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their derivatives.
F. Ji, X. Li, W. Guo, W. Wu, H. Jiang, J. Org. Chem., 2015, 80, 5713-5718.
A palladium-catalyzed C-H carbonylation of benzylamines provides isoindolinone scaffolds in good yields under gas-free conditions by using benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate.
L-Y. Fu, J. Ying, X. Qi, J.-B. Peng, X.-F. Wu, J. Org. Chem., 2019, 84, 1238-1246.
In a palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides, an imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials with high atom- and step-economy in a one-pot manner.
F. Ji, J. Li, X. Li, W. Guo, W. Wu, H. Jiang, J. Org. Chem., 2018, 83, 104-112.
The use of Cu(OAc)2 enables a dehydrogenative cross-coupling between two heteroarenes via disproportionation of the copper mediator. This synthetic protocol provides a concise and "green" access to unsymmetrical biheteroarenes bearing structural motifs of substantial utility in organic synthesis.
Z. F. Mao, Z. Wang, Z. Q. Xu, F. Huang, Z. K. Yu, R. Wang, Org. Lett., 2012, 14, 3854-3857.