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winter11_5 - Project Werner R eport Report Format Standard...

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Project Werner Report February 11, 2011
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Synthesis and Characterization of Iron Derivatives Having a Pyridine-Linked Bis(anilide) Pincer Ligand Edward C. Weintrob, Daniel Tofan, and John E. Bercaw* Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, Pasadena, California 91125 Received January 15, 2009 A pyridine-linked bis(aniline) pincer ligand, [ 2 ]H 2 ([ 2 ]H 2 ) (2,6-NC 5 H 3 (2-(2,4,6-Me 3 C 6 H 2 )-NHC 6 H 4 ) 2 ), has been synthesized in two steps. Deprotonation with Me 3 SiCH 2 Li followed by metalation with FeCl 2 yielded a LiCl adduct of [ 2 ]Fe. The complex is freed of LiCl with excess TlPF 6 or by crystallization from toluene/petroleum ether, giving [ 2 ]Fe(THF). [ 2 ]Fe(THF) reacts with I 2 and O 2 to generate [ 2 ]FeI and ([ 2 ]Fe) 2 O, respectively. The complexes have been characterized by 1 H NMR spectroscopy, elemental analysis, X-ray crystallography, and UV - vis spectroscopy. [ 2 ]Fe(THF) has been examined using cyclic voltammetry. Introduction Noble metals have been dominant in many areas of catalytic organic transformations: a fact that may be partially due to their readily accessible two electron redox couples, as well as their oxygen, water, and functional group tolerance. 1 These abilities are counterbalanced, however, by those same metals’ cost, and in some cases by environmental or toxicological considerations. By comparison, iron is cheap, relatively nontoxic, and environmentally benign. 2 For these reasons, this decade has seen an emergence of research in areas not historically associated with iron, 3 - 6 including hydrogenation, 7 - 13 hydrosilation, 8 hydrodefluorination, 14 and cross-coupling. 15 - 17 Additionally, the well-studied area of oxidation chemistry with iron complexes has made great strides in mechanistic understanding, substrate scope, chemo-, regio-, and enantioselectivity, and pertinence to industrial applications.
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