Buchwald-Hartwig Cross Coupling Reaction Reporter: Ying-Chieh CHAO Lecturer: Professor Guey-Sheng Liou Advisor: Professor Ru-Jong Jeng Data:2013/12/27.

Slides:

Advertisements

Similar presentations

Suzuki Coupling in LC Synthesis Yu Ding Nov

Advertisements

∂. ∂ Efficient Catalytic Syntheses of Organoboronate Esters Ubiquitous building blocks for the fine chemical and pharmaceutical industries NORSC Sustainable.

Amphidinolide A Isolation: 1. Kobayashi, J. et al. Tetrahedron Lett. 1986, 27, Kobayashi, J. et al. J. Nat. Prod. 1991, 54, Biological Activity:

Literature Meeting March 25, 2008 Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications David Marcoux Charette’s Laboratories.

Development of Palladium-Catalyzed C-N Bond Formation Reaction Wu Hua

Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems 杜宇鎏

CDC Reaction Involving α -C-H Bonds of Nitrogen in Amines 李南

Anion radical coupling. Plan  methods for the formation of aryl-aryl bonds  anionic cyclohydrogenation  history  mechanism  applications.

Iron-catalyzed Cross Coupling reactions: From Rust to a Rising Star

Department of Chemistry Seminar Announcement Date/Time/VenueTitle/Speaker 25 Jan (Tue) 11am – S8 Level 3 Executive Classroom Rh-Catalyzed [(5+2)+1],

Advisor ： Professor Guey-Sheng Liou Reporter ： Li-Wen Chen 合成特論期末報告 Friedel-Crafts Reaction.

1 D. A. Evans’ Asymmetric Synthesis — From 80’s Chiral Auxiliary to 90’s Copper Complexes and Their Applications in Total Synthesis Supervisor: Professor.

Catalytic Cross-coupling Reactions with Unactivated Alkyl Electrophiles and Alkyl Nucleophiles Heng Su 04/11/2008 Department of Chemistry Brandeis University.

Reporter: Yu Ting Huang Advising Prof: Ru Jong Jeng 1.

Mohammad Movassaghi,* Meiliana Tjandra, and Jun Qi Reporter: ZhiYong Han Total Synthesis of (-)-Himandrine J. AM. CHEM. SOC ASAP.

Masakatsu Shibasaki was born in 1947 in Japan. In 1974 he received his Ph. D. Degree from the University of Tokyo. After then he did postdoctoral studies.

Year 3 CH3E4 notes: Asymmetric Catalysis, Prof Martin Wills

Alkylation by Asymmetric Phase- Transfer Catalysis 张文全.

The application of alkaline metal(Ca, Sr, Ba) complex as catalyst in organic chemistry 张文全 1.

Palladium Catalyzed C-N Bond Formation Jenny McCahill

Olefin Metathesis and Use in Tandem Reactions - The Work of Marc L. Snapper James Mousseau Literature Meeting 6 May

Recent Progress in sp 3 C-H Activation Catalyzed by Palladium Bo Yao.

化学系 Department of Chemistry Catellani Reaction

The Career of Chao-Jun Li Guochang B.S. Zhengzhou University 1979 M.S. Chinese Academy of Science 1985 Tak-Hang ChanTak-Hang Chan Ph.D. McGill.

Career-in-review Keiji Maruoka Reporter: Li Chen Supervisor: Prof. David Zhigang Wang

Wangqing Kong Zhu’s group meeting 13 th, Aug, 2015 Intramolecular Asymmetric Heck Reaction and Application in Natural Products Synthesis.

Chiral Concave N-Heterocyclic Carbenes 3 rd International Summer School “Supramolecular Systems in Chemistry and Biology“ Tim Reimers Kiel, GER.

1 CATALYTIC ASYMMETRIC NOZAKI- HIYAMA-KISHI REACTION: ROLE OF ORGANOCHROMIUM COMPOUNDS AND NOVEL SALEN LIGANDS A RKAJYOTI C HAKRABARTY Prof. Uday Maitra’s.

Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins Via an Ene Reaction / [2,3]-Rearrangement Hongli Bao & Uttam K. Tambar Guillaume.

Molecular and Gold Nanoparticles Supported N-Heterocyclic Carbene Silver(I) Complexes – Synthesis, Characterization and Catalytic Applications 學生 :王趙增.

1 Molecular and Gold Nanoparticles Supported N-Heterocyclic Carbene Silver(I) Complexes – Synthesis, Characterization and Catalytic Applications 學生 : 王趙增.

Catalytic Asymmetric Total Syntheses of Quinine and Quinidine Izzat T. Raheem, Steven N. Goodman, and Eric N. Jacobsen J. Am. Chem. Soc. 2004, 126, 3,

Total Synthesis of Communesins Jian-Zhou Huang

Chem 1140; Ring-Closing Metathesis (RCM) and Ring-Opening Metathesis (ROMP) Introduction RCM Cross-Metathesis ROMP.

Synthesis of meso-substituted porphyrins

Ye Zhu 09/02/10 Burgess’s Group Meeting Chiral Ligands On A Spiro Scaffold for Transition-Metal- Catalyzed Asymmetric Reactions Work by Prof. Zhou Qi-Lin.

Supervisor: Yong Huang Reporter: Qian Wang Date: Magical Chiral Spirobiindane Skeletons.

Atom-Economical and Sustainable C-N Bond Formation Reactions from Alcohols and N-Sources via Catalytic Hydrogen Transfer Reactions September 15th, 2015.

Asymmetric BINOL-Phosphate Derived Brønsted Acids: Development and Catalytic Mechanism Reporter: Song Feifei Supervisor: Prof. Yong Huang

Rhodium-Catalyzed Chemo- and Regioselective Decarboxylative Addition of β- Ketoacids to Allenes: Efficient Construction of Tertiary and Quaternary Carbons.

Organic Pedagogical Electronic Network Properties of Hydrogen Bonding Created by Max Taggart Edited by Margaret Hilton Honors Organic Chemistry Chem 2321.

Regioselective reactions of 3,4-pyridynes enabled

The Work Of Pr Karl A. Scheidt Group Department of Chemistry, Northwestern UniVersity, Evanston.

Redox Neutral Reactions Wang Chao Redox Economy and Redox Neutral Reactions: Angew. Chem. Int. Ed. 2009, 48, 2854 – 2867.

Light and Palladium Induced Carbonylation Reactions of Alkyl Iodides Mechanism and Development Pusheng Wang Gong Group Meeting April 12 th 2014.

Organic Pedagogical Electronic Network An Introduction to Catalytic Nitrene C–H Oxidation Ashley M. Adams, Justin Su, And J. Du Bois.

Recycling the Waste: The Development of a Catalytic Wittig Reaction Angew. Chem. Int. Ed. 2009, 48, 6836 –6839.

Michael J. Krische B.S.in Chemistry from University of California at Berkeley (1989) Fulbright Fellow at Helsinki University (1990) Ph.D. in Chemistry.

Reporter: Yang Chao Supervisor: Prof. Yong Huang The Transformation of α ‑ Diazocarbonyl Compounds.

C-H Insertion Story Justin Du Bois associate professor : University of Stanford B.S. : University of California at Berkeley (1992) Ph.D. : California Institute.

Catalytic Synthesis of α,β- Unsaturated Carbonyl Derivatives 陈殿峰

Reporter: Qinglan Liu Supervisor: Prof. Yong Huang

Nicolas Gaeng Group seminar – LSPN – 30/04/15. Structures with multiple rings connected through one atom Nomenclature proposed by Adolf Baeyer in 1900.

Enantioselective Reactions Catalyzed by Iron Complexes Pablo Pérez.

Selected examples of Domino Reactions in Total Synthesis Dagoneau Dylan Zhu Group Frontiers in Chemical Synthesis May 22 th, 2014.

Ynamides : Synthesis, Reactivity and Applications

Matthew Cipolla Honors Undergraduate Research Conference

Recent Development in Isocyanide-Based

Transition Metal Catalyzed Amide Bond Formation

Guillaume Benoit – Charette Group

Superbisor: Yong Huang

Cu Catalyzed Cross Coupling

学堂讲座通知化学系 Prof. Liming Zhang 加州大学Santa Barbara分校

HONORS AND AWARDS 时间： :30 地点：礼东二楼报告厅 TITLE

Baeyer-Villiger Oxidation: Mechanism and Enantioselective Systems

Chemoselective and Regioselective Oxidative

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes

Copper Catalyzed C-N Bond Formation Using O-Acyl Hydroxylamine

1. Palladium Catalyzed Organic Transformations

The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans Kevin W. Anderson, Takashi Ikawa, Rachel E. Tundel,

Presentation transcript:

Buchwald-Hartwig Cross Coupling Reaction Reporter: Ying-Chieh CHAO Lecturer: Professor Guey-Sheng Liou Advisor: Professor Ru-Jong Jeng Data:2013/12/27 Pd-Catalyzed Amination 1

 Stephen L. Buchwald(1955-)  He entered Harvard University as a National Science Foundation Predoctoral Fellow in 1977 and received his Ph.D. in  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

 John F. Hartwig(1964-) University of California, Berkeley  A.B. Princeton University, 1986  Ph.D. University of California, Berkeley, 1990  American Cancer Society Postdoctoral Fellow, Massachusetts Institute of Technology, research focuses on the discovery and understanding of new reactions catalyzed by transition metal complexes. 3

Synthesis of the aromatic amine of history  Disadvantages Cumbersome step Harsh reaction conditions T. Migita et al., Chem. Lett., 1983, 927. P.E. Fanta et al., Synthesis, 1974, 9.  Disadvantages Chlorobenzene and iodobenzene can not react Water and heat sensitive 4

S. Buchawald et al., J. Am. Chem. Soc., 1994, 116, S. L. Buchwald et al., Angew. Chem. Int. Ed., 1995, 34, J. F. Hartwig et al., Tetrahedron lett., 1995, 36, Synthesis of the aromatic amine of history 5

Buchwald-Hartwig Cross Coupling Reaction 6 S. L. Buchwald et al., Angew. Chem. Int. Ed., 1995, 34, J. F. Hartwig et al., Tetrahedron lett., 1995, 36, 3609.

7 Can’t castylst for chlorobenzene Mondentate ligands M. Tanaka et al. M. Tanaka Tetrachedron lett. 1997, 38, Y. Kioe Tetrahedron lett. 1998, 39, 617.  Advantages Can reacted under mild condition Reduced the amount of catalyst Reduced formation of byproducts  Disadvantages P(t-Bu) 3 is air-sensitive Electron-rich monodendate phosphine ligands S. L. Buchwald et al., Angew. Chem. Int. Ed., 1999, 38, S. L. Buchwald et al., Angew. Chem. Int. Ed., 1999, 38, S. L. Buchwald et al., J. Am. Chem. Soc., 2003, 125,  Advantages Can react at room temperature Not air-sensitive

8 Chelating phosphane ligands Common inorganic base: t-BuONa, t-BuOK, NaOCH 3, K 2 CO 3, K 3 PO 4, NaOH, LHMDS, Cs 2 CO 3. Base Common organic base: DBU, MTBD. strong base is suitable Mondentate ligands and Electron-rich monodendate phosphine ligands. ex. t-BuONa. weak base is suitable Chelating phosphane ligands. ex. K 2 CO 3. L. S. Buchwald et al., Tetrahedron lett., 1997, 38, L. S. Buchwald et al., Tetrahedron, 1996, 52, 7525.

9 Solvent Common solvent: toluene, xylene, THF, DME, Dioxane, DMF, NMP, DMSO. J. F. Hartwig et al., J. Org. Chem., 2002, 67, J. M. McNamara et al., Org. Lett., 2002, 4, Most of this reaction catalysts and ligands for water and oxygen sensitive.

10 J. F. Hartwig et al., Org. Lett., 2008, 10, %

11 S. L. Buchwald et al., J. Am. Chem. Soc., 2010, 132,

12 J. F. Hartwig et al., J. Am. Chem. Soc., 2009, 131,

13 S. L. Buchwald et al., J. Am. Chem. Soc., 2008, 130, Z. Zhang et al., Synlett, 2011, S. L. Buchwald et al., J. Org. Chem., 2006, 71, W. Song et al., Org. Lett., 2011, 13,

water-containing solvent systems 14 Thank you for your attention!! G. Boche et al., Chem. Commun., 1998, BINAS-6