Categories: C-C Bond Formation > Carbocyclic compounds > Cycloalkanes
Synthesis of cyclohexanes
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Name Reactions
Conia-Ene Reaction
Recent Literature
A rhodium-catalyzed transfer hydrogenation of functionalized arenes in the
presence of tetrahydroxydiboron offers good functional group tolerance, operational simplicity and controllable chemoselectivity. The
general applicability of this procedure is demonstrated by the selective
hydrogenation of a range of arenes, including functionalized benzenes, biphenyls,
and polyaromatics.
Y. Wang, Z. Chang, Y. Hu, X. Lin, X. Dou, Org. Lett., 2021, 23,
1910-1914.
CuCl2 catalyzes a coupling of unactivated C(sp3)-H
bonds of numerous feedstock chemicals with electron-deficient olefins. The
active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to
enable the generation of a chlorine radical which acts as a powerful hydrogen
atom transfer reagent capable of abstracting strong electron-rich C(sp3)-H
bonds.
S. M. Treacy, T. Rovis, J. Am. Chem. Soc.,
2021, 143, 2729-2735.
N-heterocyclic carbenes catalyze intramolecular β-alkylations of
α,β-unsaturated esters, amides, and nitriles that bear pendant leaving groups to
form a variety of ring sizes. The mechanism is discussed.
C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc.,
2006, 128, 1472-1473.
An intramolecular iodo-aldol cyclization of prochiral α-substituted enoate
aldehydes and ketones produces hetero- and carbocycles containing quaternary centers adjacent
to secondary or tertiary centers. The reactions occur in good yields and are
highly trans-selective with hydroxyl and iodomethyl
groups on opposite faces of the ring system.
F. Douelle, A. S. Capes, M. F. Greaney, Org. Lett., 2007,
9, 1931-1934.
The combination of Pd(PPh3)2Cl2 with Xantphos
efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl
heteroarenes with aliphatic N-(acyloxy)phthalimides under irradiation of
blue LEDs at room temperature. A broad scope of secondary, tertiary, and
quaternary carboxylates, including α-amino acid derived esters, can be converted
with high stereoselectivity.
G.-Z. Wang, R. Shang, Y. Fu, Org. Lett.,
2018, 20, 888-891.
