个人简介
Stephen L. Buchwald was born (1955) in Bloomington, Indiana. He received his Sc.B. degree from Brown University in 1977 where he worked with Kathlyn A. Parker and David E. Cane at Brown University as well as Professor Gilbert Stork at Columbia University. He entered Harvard University as a National Science Foundation Predoctoral Fellow in 1977 and received his Ph.D. in 1982. His thesis work, with Jeremy R. Knowles, concerned the mechanism of phosphoryl transfer reactions in chemistry and biochemistry. He then was a Myron A. Bantrell postdoctoral fellow at Caltech with Professor Robert H. Grubbs where he studied titanocene methylenes as reagents in organic synthesis and the mechanism of Ziegler-Natta polymerization. In 1984 he began as an assistant professor of chemistry MIT. He was promoted to the associate professor (1989) and to Professor (1993) and was named the Camille Dreyfus Professor in 1997. In July 2015, he became Associate Head of the Chemistry Department at MIT. During his time at MIT he has received numerous honors including the Harold Edgerton Faculty Achievement Award of MIT, an Arthur C. Cope Scholar Award, the 2000 Award in Organometallic Chemistry from the American Chemical Society and a MERIT award from the National Institutes of Health. He has also been the recipient of the Bristol-Myers Squibb Distinguished Achievement Award and the CAS Science Spotlight Award, both received in 2005 and the American Chemical Society's Award for Creative Work in Synthetic Organic Chemistry as well as the Siegfried Medal Award in Chemical Methods which Impact Process Chemistry, both received in 2006. In 2010 he received the Gustavus J. Esselen Award for Chemistry in the Public Interest. He received the 2013 Arthur C. Cope Award from the American Chemical Society. In 2014 he was the recipient of the Linus Pauling Medal Award and the Ulysses Medal (University College Dublin). In 2015 he received an honorary doctoral degree from the University of South Florida, and also received the BBVA Frontiers in Knowledge Award in Basic Sciences (2014 Award). He was selected to receive the 2016 William H. Nichols Medal and most recently in 2018, he is the recipient of the Roger Adams Award in organic chemistry. In 2000, he was elected as a fellow of the American Academy of Arts and Sciences and in 2008 he was elected as a member of the National Academy of Science. He is the coauthor of over 490 published or accepted papers and 47 issued patents. He serves as a consultant to a number of companies and is an associate editor of Advanced Synthesis and Catalysis.
研究领域
Bioconjugation
The selective modification of complex biological molecules holds great promise for the develoment of new, potent therapies for a wide range of diseases. Our lab is currently exploring new methods for rapid, efficient, and selective modification for an array of complex, biologically important molecules.
Carbon-Nitrogen and Carbon–Oxygen Bond Formation
Amines, aryl ethers, and other nitrogen or oxygen containing functional groups are prevalent and essential constituents of many pharmaceuticals and other biologically active compounds. We are currently pursuing the development of new, highly active catalyst systems for both carbon-nitrogen (C–N) bond formation and carbon-oxygen (C–O) bond formation.
Carbon–Carbon Bond Formation
Transition metal-catalyzed systems offer a straightforward route for the formation of carbon−carbon bonds. Suzuki−Miyaura, Heck, and Negishi cross coupling are all classical methods for introducing molecular complexity and for simplifying the synthesis of desired targets. Our lab is interested in the continued development of systems for carbon−carbon bond formation. Much of this work relies on the practicality and robustness of the approach, which is often achieved through mechanistic understanding, ligand design and catalyst development.
Carbon–Fluorine Bond Formation
The development of methods for the construction of organofluorine compounds is of great importance due to the broad presence of fluorine in pharmaceuticals and agrochemicals. Fluorine substitution markedly changes the properties and behavior of the molecule (i.e. lipophilicity, cell membrane permeability, drug potency, and half-life time in the body). Thus, significant efforts have been made towards the development of new fluorination systems.
Continuous Flow Synthesis
The development of safe, scalable processes is critically important for the manufacture of pharmaceuticals. Our lab is actively engaged in the development of new continuous flow processes.
Copper–Hydride Chemistry
Catalysts that are derived from earth-abundant materials and display unique reactivity are of interest to the synthetic and the chemistry community as a whole. Although copper(I) hydride was discovered in the 1840s and widely applied in organic synthesis since the 1980s, the potential of a catalytic system has not been fully realized, and several reports in the past few years have demonstrated the applicability of this area of work. Our laboratory is interested in discovering new processes and applications that are catalyzed by copper(I) hydride complexes.
近期论文
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Y. Ye; S.T. Kim; J. Jeong; M.H. Baik; S.L. Buchwald CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence J. Am. Chem. Soc. 2019 Link
R.Y. Liu; Y. Zhou; Y. Yang; S.L. Buchwald Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct J. Am. Chem. Soc. 2019 Link
X.J. Dai; O.D. Engl; T. León; S.L. Buchwald Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles Angew. Chem. Int. Ed. 2019 Link
M.R. Uehling; R.P. King; S.W. Krska; T. Cernak; S.L. Buchwald Pharmaceutical diversification via palladium oxidative addition complexes Science 2019 Link
D.T. Cohen; C. Zhang; C.M. Fadzen; A.J. Mijalis; L. Hie; K.D. Johnson; Z. Shriver; O. Plante; S.J. Miller; S.L. Buchwald; B.L. Pentelute A chemoselective strategy for late-stage functionalization of complex small molecules with polypeptides and proteins Nat. Chem. 2019 Link
B. Pentelute; C. Zhang; E. Vinogradova; A. Spokoyny; S. Buchwald Arylation Chemistry for Bioconjugation Angew. Chem. Int. Ed. 2018 Link
S. Guo; J.C. Yang; S.L. Buchwald A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination J. Am. Chem. Soc. 2018 Link
A.A. Thomas; K. Speck; I. Kevlishvili; Z. Lu; P. Liu; S.L. Buchwald Mechanistically Guided Design of Ligands that Significantly Improve the Efficiency of CuH-Catalyzed Hydroamination Reactions J. Am. Chem. Soc. 2018 Link
K.M. Khan; Y. Zhao; T. Scully; S.L. Buchwald Catalytic Arylhydroxylation of Dehydroalanine in Continuous Flow for Simple Access to Unnatural Amino Acids Chem. Eur. J. 2018 Link
S. Ichikawa; S. Zhu; S.L. Buchwald A Modified System for the Synthesis of Enantioenriched N‐Arylamines through Copper‐Catalyzed Hydroamination Angew. Chem. Int. Ed. 2018 Link
Y. Zhou; O.D. Engl; J.S. Bandar; E.D. Chant; S.L. Buchwald CuH‐Catalyzed Asymmetric Hydroamidation of Vinylarenes Angew. Chem. Int. Ed. 2018 Link
R.Y. Liu; S.L. Buchwald Copper-Catalyzed Enantioselective Hydroamination of Alkenes Org. Syn. 2018 Link
M.W. Gribble; S. Guo; S.L. Buchwald Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile J. Am. Chem. Soc. 2018 Link
J.M. Dennis; N.A. White; R.Y. Liu; S.L. Buchwald Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common, Soluble Base in C–N Coupling J. Am. Chem. Soc. 2018 Link
H. Zhang; P. Ruiz-Castillo; S.L. Buchwald Palladium-Catalyzed C–O Cross-Coupling of Primary Alcohols Org. Lett. 2018 Link
W. Huang; M. Einzinger; T. Zhu; H.Sik Chae; S. Jeon; S.G. Ihn; M. Sim; S. Kim; M. Su; G. Teverovskiy; T. Wu; T. Van Voorhis; T.M. Swager; M.A. Baldo; S.L. Buchwald Molecular Design of Deep Blue Thermally Activated Delayed Fluorescence Materials Employing a Homoconjugative Triptycene Scaffold and Dihedral Angle Tuning Chem. Mater. 2018 Link
K. Kubota; P. Dai; B.L. Pentelute; S.L. Buchwald Palladium Oxidative Addition Complexes for Peptide and Protein Crosslinking J. Am. Chem. Soc. 2018 Link
E. Tsai; R.Y. Liu; Y. Yang; S.L. Buchwald A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes J. Am. Chem. Soc 2018 Link
R.Y. Liu; M. Bae; S. L. Buchwald Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes J. Am. Chem. Soc. 2018 Link
Y. Zhou; J.S. Bandar; R.Y. Liu; S.L. Buchwald CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes J. Am. Chem. Soc 2018 Link
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