By Dyker G. (ed.)
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Extra resources for Handbook of C-H Transformations.. Applications in Organic Synthesis
Hessel, W. Ehrfeld, K. Golbig, C. Hofmann, S. Jungwirth, H. Löwe, T. Richter, M. Storz, A. Wolf, O. Wörz, J. Breysee, in, Proc. 3rd Int. Conf. Microreaction Technology, 1999, Springer, Berlin, 151 67 Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393 68 K. Jähnisch, M. Baerns, V. Hessel, Angew. Chem. Int. Ed. 2004, 43, 406 27 29 II C–H Transformation at sp-Hybridized Carbon Atoms Handbook of C–H Transformations. ) Copyright 2005 WILEY-VCH Verlag GmbH & Co. 1 Recent Developments in Enantioselective Addition of Terminal Alkynes to Aldehydes Tobias Ritter and Erick M.
The selectivity of alkane oxidations can be improved by using oxygen and NHPI (N-hydroxyphthalimide; Table 7, entry 54), often in the presence of a cobalt catalyst under mild conditions . By using NHPI, which forms PINO (phthalimide-N-oxyl) radicals in situ, adamantane can be oxidized to adamantanol with 52 % yield . Classical reagents, for example H2O2/O2, lead to a mixture of adamantanol and adamantanal (Table 7, entry 55) . Another approach to selective photochemical oxidation of cyclic alkanes is the oxidation of cyclohexane (Table 7, entry 56) using zeolite NaY and leading to conversion of 40 % .
This elegant approach generates an active oxygen species which is inserted into the C–H bond. Thus highly selective oxygen is generated on the catalyst. The amount of free oxygen in the gas phase is on a very low level and attack of the aromatic ring and total oxidation is minimized. The catalyst must be regenerated periodically, because of deactivation after coke-formation. Though the yield and selectivity of the process are high and only one step is required for conversion of benzene, it is not yet commercialized.
Handbook of C-H Transformations.. Applications in Organic Synthesis by Dyker G. (ed.)