Department of Chemistry

Yale University

Our work is aimed at understanding how transition metal complexes and organometallic compounds can be used to control the stereochemistry of organic reactions.

Current topics of interest are: asymmetric catalysis; asymmetric catalysis using racemic catalysts and chiral inhibitors (chiral poisoning) or chiral accelerants; X-ray crystallography; nmr spectroscopy; fluxional and stereochemically nonrigid molecules (particularly 16-electron species), nmr of paramagnetic molecules; stereochemistry of organometallics; mechanisms of inorganic and organometallic reactions; electronic control of stereochemistry in reactions of organometallics; organometallic reagents for organic synthesis; pseudoenantiomeric complexes; kinetic resolutions, spontaneous resolution, asymmetric transformations, quasi-racemates; and single source molecular precursors for semiconductor nanocrystals and quantum dots.

A summary of our earlier work can be found in:

Controlling stereochemistry in C-C and C-H bond formation with electronically asymmetric organometallics and chiral poisons, J.W. Faller, M.R. Mazzieri, J.T. Nguyen, J. Parr, and M. Tokunaga, Pure & Appl. Chem.1994, 66, 1463-9.

Recent publications:

Chiral Poisoning and Asymmetric Activation, J. W. Faller, J. Parr, A. Lavoie, Chem. Rev. 2003, 103, 3345-3367.

Stereochemical Nonrigidity: Organometallic Compounds, J.W. Faller, in Encyclopedia of Inorganic Chemistry, R.B. King (ed), 2^nd ed, John Wiley and Sons, 2005, pp 5270-5303.

Lewis Acid Catalysis by Ruthenium Complexes, J. W. Faller, J. Parr, Current Organic Chemistry, 2006 10 , 151-163.

Dynamic NMR Spectroscopy in Organometallic Chemistry, J. W. Faller, in Comprehensive Organometallic Chemistry III , Edited by R. H. Crabtree and D. M. P. Mingos, Elsevier, Oxford, 2006, vol 1, pp. 407-428.

Diastereoselectivity in Chiral Ruthenium Complexes of Chiraphos Monoxide Ligands: Epimerization, Quasiracemates and Lewis Acid Catalysis, J.W. Faller, X. Liu, J. Parr, Chirality, 2000 12, 325-337.

Synthesis, Characterization, Diastereoselectivity and Catalytic Activity of Complexes of Ruthenium with BINAP Monoxide. J.W. Faller, J. Parr Organometallics, 2000, 19, 1829-1832. (NOTE: We have now found conditions that improve the ee to >95%, J. Am. Chem. Soc., 2001, 123, 2575-2529.)

Diastereoselectivity in Chiral Osmium Complexes of a Bidentate Bisphosphine Monoxide Ligand, J.W. Faller, Jonathan Parr, Organometallics, 2000, 19, 3556-3561.

Diastereoselective Synthesis and Electronic Asymmetry of Chiral Nonracemic Re(V) Oxo Complexes Containing the Hydrotris(1-pyrazolyl)borate Ligand , J.W. Faller, A. R. Lavoie, Organometallics, 2000,19, 3957-3962

Pyridine Adducts of Chiral Arene Ruthenium Compounds. Diastereoselective Synthesis and Characterization, J. W. Faller, B. J. Grimmond and M. Curtis, Organometallics. 2000, 19, 5174-5181.

Reversible alpha-Elimination in the Conversion of N--CH to N--CH=Ir by Double C-H Activation, D-H. Lee, J. Chen, J. W. Faller, and R. H. Crabtree, Chem. Commun. 2001, 213-214.

Utility of Osmium(II) in the Catalysis of Asymmetric Diels-Alder Reactions, J.W. Faller, J. Parr, Organometallics, 2001, 20, 697-699.

The Synthesis of New Complexes of Rhenium(I) with Heterotridentate [P,N,O] Ligands, J. W. Faller, G. Mason and J. Parr, J. Organometal. Chem.2001,626, 181-185.

Application of Electronic Asymmetry to Highly Enantioselective Catalytic Diels-Alder Reactions, J. W. Faller, B. J. Grimmond, and D. D'Allessi, J. Am. Chem. Soc., 2001, 123, 2575-2529.

A New Chiral at Metal Catalyst containing QUINAP for Enantioselective Diels-Alder Reactions, J. W. Faller, B. Grimmond, Organometallics, 2001, 20, 2454-2458.

Highly Enantioselective Diels-Alder Catalysis With a Chiral Ruthenium Bisoxazoline Complex, J. W. Faller and A. Lavoie, J. Organometal. Chem., 2001, 630, 17-22

Abnormal binding in a carbene complex formed from an imidazolium salt and a metal hydride complex, S. Gründemann, A. Kovacevic, M.Albrecht, J. W. Faller, R. H. Crabtree, Chem. Commun. 2001, 2274-2275.

Rearrangements in Allyl Palladium Complexes with Hemilabile Chelating Ligands, J. W. Faller, H. L. Stokes-Huby and M. A. Albrizzio, Helv. Chim. Acta , 2001, 84, 3031.

Enantioselective routes to both enantiomers of aryl alcohols with a single catalyst antipode: Ru and Os transfer hydrogenation catalysts, J. W. Faller, A. Lavoie, Org. Lett. 2001, 3, 3703-3706.

Catalysts for the Asymmetric Transfer-Hydrogenation of Ketones Derived from (L)-Prolinamide and (CymeneRuCl₂)₂ or (Cp*RhCl₂)₂ , J. W. Faller, A. Lavoie, Organometallics, 2001, 20, 5245-5247.

Tridentate carbene CCC and CNC pincer Pd complexes: structure, fluxionality and catalytic activity S. Gründemann, M. Albrecht, J. A. Loch, J. W. Faller, R. H. Crabtree, Organometallics, 2001, 20, 5485-5488.

Palladium Complexes With Tridentate Pincer Bis-Carbene Ligands as Efficient catalysts for C-C Coupling , J. A. Loch,M. Albrecht, E. Peris, J. Mata, J.W. Faller, and R. H. Crabtree, Organometallics, 2002, 21, 700-706.

Tunable Stereoselective Hydrosilylation of PhCCH Catalyzed by Some Cp*Rh Complexes, J. W. Faller and D. G. D'Alliessi Organometallics, 2002, 21, 1743-1746.

An Application of the Chiral Poisoning Strategy: Enantioselective Diels-Alder Catalysis with a Racemic Ru/BINAP-Monoxide Lewis Acid, J. W. Faller, A. R. Lavoie, B. J. Grimmond Organometallics, 2002, 21, 1662-1666.

A General Strategy for Improving Enantiomeric Purities via the Tandem Use of Mirror-Image Catalysts, J. W. Faller, A. Lavoie, Organometallics, 2002, 21, 2010-2012.

Complexes of elements of group 9 and 10 with new chiral chelating bisphosphine monosulfide and monoselenide ligands, J. W. Faller, J. Lloret-Fillol and J. Parr, New J. Chem. 2002 26, 883-888.

Enantioselective Syntheses of Nonracemic Benzyl-a-d alcohols via Catalytic Transfer-Hydrogenation with Ru, Os, Rh, and Ir Catalysts, J. W. Faller, A. R. Lavoie, Organometallics, 2002, 21, 3493-3495.

Interplay of weak interactions: An iridium(III) system with an agostic tert-butyl but a nonagostic isopropyl group, E. Clot, O. Eisenstein, T. Dube, J. W. Faller, R. H. Crabtree, Organometallics, 2002, 21, 575-580.

Chelated iridium(III) bis-carbene complexes as air-stable catalysts for transfer hydrogenation, Albrecht, M.; Miecznikowski, J. R.; Samuel, A.; Faller, J. W.; Crabtree, R. H., Organometallics 2002, 21, 3596-3604.

A cis-IrL(CO) Group Responds to Increasing Steric Bulk of L by M-L Stretching, not M-C-O Tilting or Bending. T. Dubé, J. W. Faller and R. H. Crabtree, Inorg. Chem. 2002, 41, 5561-5565

Bis-carbene complexes from oxidative addition of imidazolium C- H bonds to palladium(0), , S. Grundemann, M. Albrecht, A. Kovacevic, J. W. Faller, R. H. Crabtree, J. Chem. Soc.-Dalton Trans. 2002, 2163-2167.

Abnormal ligand binding and reversible ring hydrogenation in the reaction of imidazolium salts with IrH₅(PPh₃)₂, Grundemann S, Kovacevic A, Albrecht M, Faller J. W., Crabtree RH, J. Am. Chem. Soc. 2002, 124, 10473-10481.

Palladium-Catalyzed Cross-Coupling Reactions of Allyl, Phenyl, Alkenyl and Alkynyl Germatranes with Aryl Iodides, J.W. Faller, R. G. Kultyshev, Organometallics 2002, 21, 5911-5918.

Alkynyl germatranes as alternative reagents for the preparation of biarylethynes, J.W. Faller, R. G. Kultyshev, J. Parr, Tetrahedron Lett. 2003, 44, 451-453.

One-Step Syntheses of Styryl and Allyl Germatranes via Rhodium or Palladium-Catalyzed Hydrogermylation of Arylacetylenes by HGe(OCH₂CH₂)₃N, J.W. Faller, R. G. Kultyshev, Organometallics 2003, 22, 199-202.

Outer sphere anion participation can modify the mechanism for conformer interconversion in Pd pincer complexes, J.R. Miecznikowski, S. Gründemann, M. Albrecht, C. Mégret, E. Clot, J.W. Faller, O. Eisenstein, and R.H. Crabtree J. Chem. Soc., Dalton, 2003, 831-838.

Nonrigid Diastereomers: Epimerization at chiral metal centers or chiral ligand conformations?, J. W. Faller, A. Lavoie, J. Parr, New J. Chem., 2003, 27, 899-901.

Planar Chirality in Tethered eta⁶:eta¹-(Phosphinophenylenearene-P)ruthenium(II) Complexes and Their Potential Use as Asymmetric Catalysts, J. W. Faller, D. G. D'Alliessi, Organometallics, 2003, 22, 2749-2757.

Rhodium and iridium complexes of N-heterocyclic carbenes via transmetalation: Structure and dynamics, Chianese, A. R.; Li, X. W.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663-1667.

Chiral Poisoning and Asymmetric Activation, J. W. Faller, J. Parr, A. Lavoie, Chem. Rev. 2003, 103, 3345-3367.

Half-sandwich complexes of ruthenium, rhodium and iridium with a chiral bisphosphine monoselenide, Evans, S.; Faller, J. W.; Parr, J. J. Organometal. Chem. 2003, 674, 56-62.

Reactivity Differences in the Syntheses of Chelating N-Heterocyclic Carbene Complexes of Rhodium Are Ascribed to Ligand Anisotropy, Mata, A. R. Chianese, J. R. Miecznikowski, M. Poyatos, E. Peris, J. W. Faller, R. H. Crabtree, Organometallics, 2004, 23, 1253-1263.

Kinetic Resolution and Unusual Regioselectivity in Palladium-Catalyzed Allylic Alkylations with a Chiral P,S ligand, J.W. Faller, J. C. Wilt, J. Parr, Org. Lett. 2004 6, 1301-1304.

Novel Binding Modes and Hemilability in Atropisomeric Phosphino-amino Palladium Complexes, J.W. Faller, N. Sarantopoulos, Organometallics, 2004, 23, 2008-2014.

Retention of Configuration and Regiochemistry in Allylic Alkylations via the Memory Effect, J. W. Faller, N. Sarantopoulos, Organometallics, 2004, 23, 2179-2185.

Abnormal C5-Bound N-Heterocyclic Carbenes: Extremely Strong Electron Donor Ligands and Their Iridium(I) and Iridium(III) Complexes, A. R. Chianese, A. Kovacevic, B. M. Zeglis, J. W. Faller, R. H. Crabtree, Organometallics, 2004, 23, 2461-2468.

Reactivity Differences in the Syntheses of Chelating N-Heterocyclic Carbene Complexes of Rhodium Are Ascribed to Ligand Anisotropy, J. A. Mata, A. R. Chianese, J. R. Miecznikowski, M. Poyatos, E. Peris, J. W. Faller, R. H. Crabtree, Organometallics, 2004, 23, 1253-1263

Iridium(I) and Iridium(III) Complexes, A. R. Chianese, A. Kovacevic, B. M. Zeglis, J. W. Faller, R. H. Crabtree, Organometallics, 2004, 23, 2461-2468.

Dimer-of-Dimers Model for the Oxygen-Evolving Complex of Photosystem II. Synthesis and Properties of [Mn^IV ₄O₅(terpy)₄(H₂O)₂](ClO₄)₆, H. Chen, J. W. Faller, R. H. Crabtree and G. W. Brudvig, J. Am. Chem. Soc. 2004, 126, 7345-7349.

Double Geminal C-H Activation and Reversible α-Elimination in 2-Aminopyridine Iridium(III) Complexes: the Role of Hydrides and Solvent in Flattening the Free Energy Surface, E. Clot, J. Chen, D-H. Lee, S. Y. Sung, L. N. Appelhans, J. W. Faller, R. H. Crabtree, O. Eisenstein, J. Am. Chem. Soc. 2004, 126, 8795-8804.

New Synthetic Routes to Allylic Germatranes, J. W. Faller, R. G. Kultyshev, J. Parr J. Organometal. Chem. 2004, 689, 2565-2570.

Stoichiometric C-C Coupling Reactions in the Coordination Sphere of an Iridium(III) Alkyl, X. Li, L.N. Appelhans, J. W. Faller, and R. H. Crabtree, Organometallics 2004, 23, 3378-3387.

Convenient syntheses of aryl and perfluoroaryl trichlorogermanes and germatranes via an organotin route, R. G. Kultyshev, G. K. S. Prakash, G. A. Olah, J. W. Faller, J. Parr,Organometallics 2004, 23, 3184-3188.

Enantioselective Synthesis of Acyclic Allylic Esters Catalyzed by a Palladium/BINAP(S) System J.W. Faller and J. C. Wilt, Tetrahedron Lett. 2004, 45, 7613-7616.

“Strategies for Improving Enantiomeric Purities via the Tandem Use of Mirror-Image Catalysts and Controlling Reversible Epimerizations”, J. W. Faller, A. R. Lavoie, and N. Sarantopoulos, in ACS Symposium Series ed. S. V. Malhotra, Methodologies in Asymmetric Catalysis, 2004, pp 29-41.

Palladium/BINAP(S)-catalyzed asymmetric allylic amination, J. W.Faller, J. C. Wilt, Org. Lett. 2005, 7, 633-636.

Synthesis, characterization and structural investigation of new rhenium-oxo complexes containing bidentate phosphine ligands: an exploration of chirality and conformation in chelate rings of small and large bite angle ligands, M. L. Parr, C. Perez-Acosta, , J. W. Faller, New J. Chem. 2005, 29, 613-619.

Resolution and Diels-Alder Catalysis with Planar Chiral Arene-Tethered Ruthenium Complexes, J. W. Faller, P. P. Fontaine, Organometallics 2005, 24, 4132-4138

Cycloiridation of a,b-Unsaturated Ketones, Esters, and Acetophenone, X. Li, J. W. Faller, R. H. Crabtree, Organometallics 2005, 24, 4810-4815.

Regioselectivity in the Palladium/(S)-BINAP(S)-Catalyzed Asymmetric Allylic Amination: Reaction Scope, Kinetics, and Stereodynamics, J.W. Faller, J. C. Wilt, Organometallics 2005, 24, 5076-5083.

Crystallization Induced Asymmetric Transformations in Crotyl Molybdenum Complexes. J. W. Faller, N. Sarantopoulos Cryst. Growth and Design, 2005, 5, 2356-2361.

General synthesis of di-mu-oxo dimanganese complexes as functional models for the oxygen evolving complex of photosystem II, Chen, H. Y.; Tagore, R.; Das, S.; Incarvito, C.; Faller, J. W.; Crabtree, R. H.; Brudvig, G. W. Inorg. Chem. 2005, 44, 7661-7670.

Stereochemical Nonrigidity: Organometallic Compounds, J.W. Faller, in Encyclopedia of Inorganic Chemistry, R.B. King (ed), 2^nd ed, John Wiley and Sons, 2005, pp 5270-5303.

Lewis Acid Catalysis by Ruthenium Complexes, J. W. Faller, J. Parr, Current Organic Chemistry, 2006, 10, 151-163.

Ruthenium catalyzed enyne cycloisomerizations and hydroxycyclizations with skeletal rearrangement, J. W. Faller and P. P. Fontaine, J. Organometal. Chem. 2006, 691, 1912-1918.

Resolution of BIPHEP on Rh with a chiral diene auxiliary, J. W. Faller and J. C. Wilt, J. Organometal. Chem. 2006, 691, 2207-2212.

Stereodynamics and Conformational Equilibria in Some Chiral Pseudooctahedral Tungsten Crotyl Complexes, J. W. Faller and P. P. Fontaine J. Organometal. Chem. 2006, 691, 4667-4675.

Imine Hydrogenation Catalyzed by Iridium Complexes Comprising Monodentate Chiral Phosphoramidites and N-Donor Ligands, J. W. Faller, S. C. Milheiro, J. Parr, J. Organometal. Chem. 2006, 691, 4945-4955.

Stereodynamics and Asymmetric Hydrosilylation with Chiral Rhodium Complexes Containing a Monodentate N-Heterocyclic Carbene, J. W. Faller and P. P. Fontaine, Organometallics, 2006, 25, 5887-5893.

Synthesis and Characterization of a Planar Chiral and Chiral-at-Metal Ruthenium N-Heterocyclic Carbene Complex, J. W. Faller and P. P. Fontaine J. Organometal. Chem. 2006, 691, 5798-5803.

Epimerization, Diastereoselectivity and Hemilability in Dicationic Chiral Ruthenium Complexes with Bidentate (P^S) Bisphosphine Monosulfide Ligands, J.W. Faller, P. P. Fontaine, J. Organometal. Chem., 2007, 692, 976-982.

Chiral Memory Effects in Catalytic Hydrogenations with Dynamically Chiral Ligands, J.W. Faller, P. P. Fontaine, J. Organometal. Chem., 2007, 692, 1110-1117.

Stereoselectivity in a chiral ruthenium ethylene hydride complex: Evidence of an agostic intermediate, J.W. Faller, P. P. Fontaine, Organometallics 2007, 26, 1738-1743.

Hemilability and Nonrigidity in Metal Complexes of Bidentate P,P=S Donor Ligands, J. W. Faller, S. C. Milheiro, J. Parr, J. Organometal. Chem., 2008, 693, 1478-1493.

Manganese Catalysts with Molecular Recognition Functionality for Selective Alkene Epoxidation, J. F. Hull, E. L. O. Sauer, C. D. Incarvito, J. W. Faller, G. W. Brudvig, R. H. Crabtree, Inorg. Chem., 2009, 48, 488-495.

Hemilability and Regioselectivity in Metal Complexes of Bidentate P^P=S Donor Ligands, J. W. Faller, T. Friss, J. Parr, J. Organometal. Chem., 2010, 695, 2644-2650.

Regioselectivity and Memory Effects in Palladium Catalyzed Allylic Alkylations with P^P=S Donor Ligands, S. Milheiro, J. W. Faller, J. Organometal. Chem., 2011, 696, 879-886.

Stoichiometric and Catalytic Reactions of Thermally Stable Nickel(0) NHC Complexes. J. Wu, J. W. Faller, N. Hazari, T. J. Schmeier, Organometallics, 2012, 31, 806-809.

Our past work was supported by National Science Foundation Grant CHE0092222. Any opinions, findings and conclusions or recommendations expressed in this material are those of the author and do not necessarily reflect the views of the National Science Foundation (NSF).

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Last updated June 2012

jack.faller@yale.edu