CHAPTER 4: Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions
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Published:19 Aug 2014
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Special Collection: 2014 ebook collection , ECCC Environmental eBooks 1968-2022 , 2011-2015 organic chemistry subject collectionSeries: Green Chemistry
C. Darcel, J. Sortais, and S. Quintero Duque, in From C–H to C–C Bonds: Cross-Dehydrogenative-Coupling, ed. C. Li, The Royal Society of Chemistry, 2014, pp. 67-92.
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In transition metal catalyzed cross-dehydrogenative-coupling (CDC) reactions for the efficient building of C–C bonds from two C–H bonds, iron is an inexpensive and earth abundant metal that has attracted increasing interest during the last few years. Using commercially available iron salts (such as FeCl3, FeCl2, Fe(OAc)2), or organometallic precursors (such as Fe2(CO)9) as catalysts, in the presence of stoichiometric amounts of oxidants such as tert-butyl hydroperoxide, di-tert-butyl peroxide, DDQ, TEMPO oxoammonium salts, or even oxygen, sp3– sp3, sp3–sp2, sp3–sp and sp2–sp2 C–C bond formation can be efficiently performed. This is a breakthrough in terms of greener chemistry! Interestingly, this iron-catalyzed methodology also allows more sophisticated heterocyclic and/or polycyclic compounds to be prepared in tandem sequences.