John Hartwig

Professor John Hartwig


Department of Chemistry,
University of Illinois,
Box 58-6 CLSL A410,
600 South Mathews Ave.,
Urbana, IL  61801, USA;
Ph. (217) 244-7652;
email: This e-mail address is being protected from spambots. You need JavaScript enabled to view it ;
ww.scs.uiuc.edu/hartwig

Education

 1990-1992 Massachusetts Institute of Technology, Cambridge, MA
Postdoctoral Advisor: Prof. Stephen J. Lippard
 Studied the Pt-DNA adducts formed by an orally active platinum antitumor drug
 1986-1990 University of California, Berkeley, CA  Ph.D., Chemistry.  
Ph.D. Advisors: Robert G. Bergman, Richard A. Andersen
Studied reactions at ruthenium-oxygen, ruthenium-nitrogen, and ruthenium-carbon bonds.
 1982-1986 Princeton University, Princeton, NJ  AB, Chemistry, High Honors; Thesis Advisor: Maitland Jones Jr;
Studied the stereochemistry of dihalocarbene additions to strained olefins.


Employment

 2006 University of Illinois, Urbana-Champaign Kenneth L. Rinehart Professor of Chemistry
 2004
 Yale University, New Haven, CT  Irénée duPont Professor of Chemistry
 1998-2004 Yale University, New Haven, CT  Professor of Chemistry
 1996-1998 Yale University, New Haven, CT  Associate Professor of Chemistry
 1992-1996 Yale University, New Haven, CT Assistant Professor of Chemistry


Awards

 2009  National Institutes of Health MERIT Award
 2009  Edward Mack Jr. Memorial Award, Ohio State University
 2009  Mitsui Chemicals Catalysis Science Award, Japan
 2009  Joseph Chatt Award of the Royal Society of Chemistry
 2009  Edward Mack Jr. Memorial Award, Ohio State University
 2009  Mitsui Chemicals Catalysis Science Award, Japan
 2008  International Association of the Catalysis Societies (IACS) Award
 2008  Paul Rylander Award of the Organic Reactions Catalysis Society
 2007  Mukaiyama Award from the Society of Synthetic Organic Chemistry, Japan
 2007  Raymond and Beverly Sackler Prize in the Physical Sciences
 2007  Tetrahedron Young Investigator Award in Organic Synthesis
 2006  ACS Award in Organometallic Chemistry
 2004  Thieme-IUPAC Prize in Synthetic Organic Chemistry
 2004  Solvias Ligand Prize
 2004  Chemical Abstract Service Science Spotlight Award
 2003  Leo Hendrik Baekeland Award from the North Jersey ACS Division
 1997  A.C. Cope Scholar Award
 1997  Eli Lilly Award Grantee
 1997  Camille Dreyfus Teacher-Scholar Award
 1996  Alfred P. Sloan Research Fellowship
 1995, 1996  Union Carbide Innovative Recognition Award
 1995  Yale University Junior Faculty Fellowship
 1994  National Science Foundation Young Investigator Award
 1992  Dupont Young Professor Award
 1992  Dreyfus Foundation New Faculty Award
 1990-1992  American Cancer Society Postdoctoral Fellow
 1990  National Institutes of Health Postdoctoral Fellowship (declined)
 1988  University of California Regents Fellow

Selected Named Lectureships

1998
  R.C. Fuson Lectureship, Urbana-Champaign, Illinois
 2000  Frontiers of Chemistry Lecturer, Kloster Seeon, Germany
 2000  Astra-Zeneca Lecture Stockholm, Sweden
 2001  Carl Ziegler Lecture Mülheim, Germany
 2001  Gerhard Closs Lectureship, University of Chicago
 2002  Roche Lecturer, University of Colorado
 2003  Karcher Lectureship, University of Oklahoma
 2003  Heidelberg Forum of Molecular Catalysis, University of Heidelberg
 2004  Sasol Lectureship, University of Ottawa
 2004  Eli Lilly Lecturer, Colorado State University
 2004  Novartis Lectureship Series
 2004  Methylgene Lecturer, University of Montreal
 2005  2005 Merck Frosst Lecturer, University of Victoria
 2005  Frank Burnett Dains Memorial Lecture, University of Kansas
 2005  Stuart Rosenfeld Lecturer, Smith College
 2006  Dalton Lectureship, University of California, Berkeley
 2006  Eli Lilly Symposium Lecturer, Harvard University
 2007  Friend E. Clark Lecturer, West Virginia University
 2008  Gassman Lecturer, University of Minnesota, Minneapolis, MN
 2008  Frontiers in Chemical Research Lecturer, Texas A&M University
 2009  Peter C. Reily Lectureship, Notre Dame, Indiana
 2009  UC Irvine-Novartis Lectureship, California
 2009
  Schulich Visiting Professor Lectureship, Technion-Israel Institute of Technology
 2009  RSC Joseph Chatt Lectureship, United Kingdom


Selected Peer-Reviewed Publications from the Past Three Years (237 publications total)
1.    Fernández-Rodríguez, M.A.; Shen, Q.L.; Hartwig, J.F. “A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols” J. Am. Chem. Soc. 2006, 128, 2180-2181.
2.    Johns, A.M.; Sakai, N.; Ridder, A.; Hartwig, J.F. “Direct Measurement of the Thermodynamics of Vinylarene Hydroamination” J. Am. Chem. Soc. 2006; 128, 9306-9307.
3.    Shekhar, S.; Ryberg, P.; Hartwig, J. F. “Oxidative addition of phenyl bromide to Pd(BINAP) vs Pd(BINAP)(amine). Evidence for addition to Pd(BINAP)” Org. Lett. 2006, 8, 851-854.
4.    Zhao, P. J.; Incarvito, C. D.; Hartwig, J. F. “Direct Observation of beta-Aryl Eliminations from Rh(I) Alkoxides” J. Am. Chem. Soc. 2006, 128, 3124-3125.
5.    Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. “Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes”, J. Am. Chem. Soc. 2006, 128, 3584-3591.
6.    Hama, T.; Culkin, D.A.; Hartwig, J.F. “Palladium-Catalyzed Intermolecular alpha-Arylation of Zinc Amide Enolates under Mild Conditions” J. Am. Chem. Soc. 2006, 128, 4976-4985.
7.    Takemiya, A.; Hartwig, J.F. “Rhodium-Catalyzed Intramolecular, Anti-Markovnikov Hydroamination. Synthesis of 3-Arylpiperidines” J. Am. Chem. Soc. 2006, 128, 6042-6043.
8.    Sakai, N.; Ridder, A.; Hartwig, J.F. “Tropene Derivatives by Sequential Intermolecular and Transannular, Intramolecular Palladium-Catalyzed Hydroamination of Cycloheptatriene” J. Am. Chem. Soc. 2006, 128, 8134-8135.
9.    Fujita, K.I.; Yamashita, M; Puschmann, F.; Alvarez-Falcon, M.M.; Incarvito, C.D.; Hartwig, J.F. “Organometallic Chemistry from Amidate Complexes. Reductive Elimination of N-Aryl Amidates from Palladium(II)” J. Am. Chem. Soc. 2006, 128, 9044-9045.
10.    Zhao, P.; Incarvito, C.D.; Hartwig, J.F. “Carbon-Oxygen Bond Formation between a Terminal Alkoxo Ligand and a Coordinated Olefin. Evidence for Olefin Insertion into a Rhodium-Alkoxide” J. Am. Chem. Soc. 2006, 128, 9642-9643.
11.    Shen, Q.; Hartwig, J. F. “Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides” J. Am. Chem. Soc. 2006 128, 10028-10029.
12.    Shekhar, S.; Trantow, B.; Leitner, A.; Hartwig, J. F. “Sequential Catalytic Isomerization and Allylic Substitution. Conversion of Racemic Branched Allylic Carbonates to Enantioenriched Allylic Substitution Products” J. Am. Chem. Soc. 2006, 128, 11770-11771.
13.    Rosenfeld, D.C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J.F. “Hydroamination and Hydroalkoxylation Catalyzed by Triflic Acid. Parallels to Reactions Initiated with Metal Triflates” Org. Lett. 2006, 8, 4179-4182.
14.    Su, W.; Raders, S.; Verkade, J.G.; Liao, X; Hartwig, J.F. “Palladium-Catalyzed alpha-Arylation of Trimethylsilyl Enol Ethers with Aryl Bromides and Chlorides. A Synergistic Effect of Two Metal Fluorides as Additives” Angew. Chem. 2006, 45, 5852-5855, VIP and cover article.
15.    Murphy, J.M.; Lawrence, J.D. Kawamura, K.; Incarvito, C.; Hartwig, J.F “Ruthenium-Catalyzed Regiospecific Borylation of Methyl C-H Bonds” J. Am. Chem. Soc. 2006, 128, 13684-13684.
16.    Takemiya, A.; Hartwig, J.F. “Palladium-Catalyzed Synthesis of Aryl Ketones by Coupling of Aryl Bromides with an Acyl Anion Equivalent” J. Am. Chem. Soc. 2006, 128, 14800-14801.
17.    Johns, A.M; Tye, J.W.; Hartwig, J.F. “Relative Rates for the Aminations of h3-Allyl and h3-Benzyl Complexes of Palladium” J. Am. Chem. Soc. 2006, 128, 16010-16011.
18.    Hartwig, J.F. “Electronic Effects on Reductive Elimination To Form Carbon-Carbon and Carbon-Heteroatom Bonds from Palladium(II) Complexes” Inorg. Chem. 2007, 46, 1936-1947. 
19.    Murphy, J.M.; Tzschucke, C.C.; Hartwig, J.F. “One-Pot Synthesis of Arylboronic Acids and Aryl Trifluoroborates by Ir-Catalyzed Borylation of Arenes” Org. Lett. 2007, 9, 757-760.
20.    Tzschucke, C.C.; Murphy, J.M.; Hartwig, J.F. “Arenes to Anilines and Aryl Ethers by Sequential Iridium-Catalyzed Borylation and Copper-Catalyzed Coupling” Org. Lett. 2007, 9, 761-764. 
21.    Zhao, P.; Incarvito, C. D.; Hartwig, J. F. “Directly Observed Transmetalation from Boron to Rhodium. Beta-Aryl Elimination from Rh(I) Arylboronates and Diarylborinates” J. Am. Chem. Soc. 2007, 129, 1876-1877.
22.    Herzon, S.B.; Hartwig, J.F. “Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines” J. Am. Chem. Soc. 2007,129, 6690-6691.
23.    Yamashita, Y.; Gopalarathnam, A.; Hartwig, J.F. “Iridium-Catalyzed, Asymmetric Amination of Allylic Alcohols Activated by Lewis Acids” J. Am. Chem. Soc. 2007, 129, 7508-7509.
24.    Weix, D.J.; Hartwig, J.F. “Regioselective and Enantioselective Iridium-Catalyzed Allylation of Enamines” J. Am. Chem. Soc. 2007, 129, 7720-7721.
25.    Shen, Q.; Hartwig, J.F. “Lewis Acid Acceleration of C-N Bond-Forming Reductive Elimination from Heteroarylpalladium Complexes and Catalytic Amidation of Heteroaryl Bromides” J. Am. Chem. Soc. 2007, 129, 7734-7735.
26.    Johns, A.M.; Liu, Z.; Hartwig, J.F. “Primary tert- and sec-Allylamines via Palladium-Catalyzed Hydroamination and Allylic Substitution with Hydrazine and Hydroxylamine Derivatives” Angew. Chem., Int. Ed. 2007, 46, 7259.
27.    Markovic, D.; Hartwig, J.F. “Resting State and Kinetic Studies on the Asymmetric Allylic Substitutions Catalyzed by Iridium-Phosphoramidite Complexes” J. Am. Chem. Soc. 2007, 129, 11680-11681.
28.    Stambuli, J.P.; Weng, Z.; Incarvito, C.D.; Hartwig, J.F. “Reductive Elimination of Ether from T-Shaped, Monomeric Arylpalladium Alkoxides” Angew. Chem., Int. Ed. 2007, 46, 7674.
29.    Murphy, J.M.; Liao, X.; Hartwig, J.F. “Meta Halogenation of 1,3-Disubstituted Arenes via Iridium-Catalyzed Arene Borylation” J. Am. Chem. Soc. 2007,129, 15434-15435.
30.    Liao, X.; Weng, Z.; Hartwig J.F. “Enantioselective-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel” J. Am. Chem. Soc. 2008, 130, 195-200.
31.    Liu, Z.; Hartwig, J.F. “Mild, Rhodium-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Olefins with Primary and Secondary Amines” J. Am. Chem. Soc. 2008, 130, 1570-1571.
32.    Ueno, S.; Hartwig, J.F. “Direct, Iridium-Catalyzed Asymmetric Allylic Etherification with Aliphatic Alcohols” Angew. Chem., Int. Ed. 2008, 47, 1928-1931.
33.    Vo, G.D.; Hartwig, J.F. “Palladium-Catalyzed a-Arylation of Aldehydes with Bromo- and Chloroarenes Catalyzed by [Pd(allyl)Cl]2 and DPPF or Q-phos” Angew. Chem., Int. Ed. 2008, 47, 2127-2130 designated as a “Hot Paper.”
34.    Shen, Q.; Ogata, T.; Hartwig, J.F. “Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides and Iodides: Scope and Structure-Activity Relationships” J. Am. Chem. Soc. 2008, 130, 6586-6596.
35.    Barrios-Landeros, F.; Carrow, B.P.; Hartwig, J.F. “Autocatalytic Oxidative Addition of PhBr to Pd(PtBu3)2 via Pd(PtBu3)2(H)(Br)” J. Am. Chem. Soc 2008, 130, 5842-5843.
36.    Boebel, T. A.; Hartwig, J. F. “Silyl-Directed, Iridium-Catalyzed ortho-Borylation of Arenes. A One-Pot ortho-Borylation of Phenols, Arylamines, and Alkylarenes” J. Am. Chem. Soc. 2008, 130, 7534-7535.
37.    Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. “Copper Complexes of Anionic Nitrogen Ligands in the Amidation and Imidation of Aryl Halide” J. Am. Chem. Soc. 2008, 130, 9971-9983.
38.    Zhou, J.; Hartwig, J.F. “Iridium-Catalyzed H/D Exchange at Vinyl Groups without Olefin Isomerization” Angew. Chem., Int. Ed. 2008, 47, 5783-5787.
39.    Zhou, J.; Hartwig, J.F. “Intermolecular, Catalytic Asymmetric Hydroamination of Bicyclic Alkenes and Dienes in High Yield and Enantioselectivity” J. Am. Chem. Soc. 2008, 130, 12220-12221.
40.    Hartwig, J.F. "Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides" Acc. Chem. Res. 2008, 41, 1534-1544.
41.    Hartwig, J.F. “Carbon–Heteroatom Bond Formation Catalysed by Organometallic Complexes” Nature 2008, 455, 314-322.
42.    Boebel, T.A.; Hartwig, J.F. “Conversion of 1,3-Disubstituted Arenes to Chiral a, a-Diaryl Methylammonium Chlorides Using Arene Borylation” Tetrahedron 2008, 64, 6824-6830.
43.    Herzon, S.B.; Hartwig, J.F. “Hydroaminoalkylation of Unactivated Olefins with Dialkylamines” J. Am. Chem. Soc. 2008, 130, 14940–14941.
44.    Alexanian, E.J.; Hartwig, J.F. “Mechanistic Study of β-Hydrogen Elimination from Organoplatinum(II) Enolate Complexes” J. Am. Chem. Soc. 2008, 130, 15627-15635.
45.    Ogata, T.; Hartwig, J.F. “Palladium-Catalyzed Amination of Aryl and Heteroaryl Tosylates at Room Temperature” J. Am. Chem. Soc. 2008, 130, 13848-13849.
46.    Madrahimov, S.T.; Markovic, D.; Hartwig, J.F. “The Allyl Intermediate in Regioselective and Enantioselective Iridium-Catalyzed Asymmetric Allylic Substitution Reactions J. Am. Chem. Soc. 2009, 131, 7228-7229.
47.    Barrios-Landeros, F.; Carrow, B.P.; Hartwig, J.F. “Effect of Ligand Steric Properties and Halide Identity on the Mechanism for Oxidative Addition of Haloarenes to Trialkylphosphine Pd(0) Complexes” J. Am. Chem. Soc. 2009, 131, 8141-8154.
48.    Alvaro, E.; Hartwig, J.F. “Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium” J. Am. Chem. Soc. 2009, 131, 7858-7868.
49.    Stanley, L.M.; Hartwig, J.F. “Regio- and Enantioselective N-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles Catalyzed by Single-Component Metallacyclic Iridium Complexes” J. Am. Chem. Soc. 2009, 131, 8971–8983.