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

Slides:

Advertisements

Similar presentations

Phenols (Ar-OH).

Advertisements

O RTHO VS I PSO : S ITE -S ELECTIVE P D AND N ORBORNENE -C ATALYZED A RENE C−H A MINATION U SING A RYL H ALIDES Zhe Dong and Guangbin Dong J. Am. Chem.

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

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

Structure and Nomenclature of Phenols

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.

Structure and properties of benzene Nomenclature of Benzene.

(-)-Kendomycin Angew. Chem. Int. Ed. 2009,48,()

Chapter 4: Aromatic Compounds

CHEMISTRY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION Dr. Sheppard CHEM 2412 Summer 2015 Klein (2 nd ed.) sections: 19.1, 19.2, 19.3, 19.4, 19.5, 19.6,

Steven Stewart Dr. Katherine Stumpo Dr. Phillip Shelton MICROWAVE-ASSISTED COMPETITIVE NITRATION OF AROMATIC COMPOUNDS.

CHAPTER 21 PHENOLS AND ARYL HALIDES NUCLEOPHILIC AROMATIC SUBSTITUTION

1 Single electron transfer reaction involving 1,3-dicarbonyl compounds and its synthetic applications Reporter: Jie Yu Oct. 31, 2009.

化学系 Department of Chemistry Catellani Reaction

何玉萍 Palladium(II)-Catalyzed Alkene Functionalization.

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

Total Synthesis of Brevenal Jon D. Rainier Department of Chemistry, University of Utah. J. Am. Chem. Soc. 2011, 133, 3208–3216.

Learning Objectives 1.Properties of phenols 2.Reaction of phenols.

Total Synthesis of Communesins Jian-Zhou Huang

Phenols Dr Md Ashraful Alam. Ar-OH Phenols are compounds with an –OH group attached to an aromatic carbon. Although they share the same functional group.

Synthesis of meso-substituted porphyrins

1 Directed ortho Metalation (DoM) of Naphthalene 1-8-bis-diethylamide: Research Towards Nerve Growth Factor Inhibitors John Stephenson †, Christopher Jones.

Reactions Involve Sulfur Ylides 陈殿峰陈殿峰

Synthesis Making molecules you want from the ones you have.

Chem 341 Review for Finals Structure Determination NMR –Chemical shifts, splitting patterns, integrations IR –ROH, C=O Formula => # of Rings + Pi-Bonds.

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

Chem. 108 Alcohols and Phenols Chapter 7.

Table 15-1, p Common Names of Carboxylic Acids Table 15.1.

Ch 19 Reactions of Benzene 1. Give the products of the following electrophilic aromatic substitution reactions. Also show how the electrophile is generated.

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.

Alcohols and Phenols 145 Chem1 King Saud University Chemistry Department.

Chapter 4: Aromatic Compounds Bitter almonds are the source of the aromatic compound benzaldehyde.

Ch. 7 Alcohols and Phenols BY MAHWASH HAFEEZ. General Formulas and Functional Groups Both of these families contain a hydroxyl group (OH) as functional.

Phenols and Aryl Halides Nucleophilic Aromatic Substitution

Group Meeting Zefan Hurley 6/9/17

Alcohols and Phenols Dr. Shatha I Alaqeel 108 Chem.

When a benzene ring is a substituent, it is called a

Organic and biochemistry

Alcohols and Phenols King Saud University Chemistry Department

Chapter 11 Phenols.

Phenol Acidity substitution effect on the acidity of phenol

Transition Metal Catalyzed Amide Bond Formation

New Chemoselective Functionalization of Nitriles and Vinylogous Esters

Superbisor: Yong Huang

ФОНД ЗА РАЗВОЈ РЕПУБЛИКЕ СРБИЈЕ

Fundamentals of Organic Chemistry

Chemoselective and Regioselective Oxidative

Fundamentals of Organic Chemistry

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes

© University of Cambridge

Theoretical Investigations of the Nature of p-p Interactions C

Phenols Ar-OH Phenols are compounds with an –OH group attached to an aromatic carbon. Although they share the same functional group with alcohols,

Ke Kong, John A. Enquist, Jr. , Monica E. McCallum, Genessa M

'III \-\- I ', I ,, - -

Generation, Study, and Application of Dicationic Intermediates

Course Number and Symbol: 108 Chem

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

sulfonyl chloride very weak base ……why?

Volume 1, Issue 6, Pages (December 2016)

Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc-pyrrolidine

Phenols 340 Chem 1st 1439.

CONTENTS  INTRODUCTION  REACTION  MECHANISM  APPLICATION  SCOPE  CONCLUSION  REFERENCE.

CONTENTS  INTRODUCTION  REACTION  MECHANISM  APPLICATION  SCOPE  CONCLUSION  REFERENCE.

Organic Chemistry CHEM 145

Presentation transcript:

The Selective Reaction of Aryl Halides with KOH: Synthesis of Phenols, Aromatic Ethers, and Benzofurans Kevin W. Anderson, Takashi Ikawa, Rachel E. Tundel, and Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

Hydrolysis of Chlorbenzene Alkali Fusion of Sodium Benzene Sulfonates

From Cumene Hydroperoid

Maleczka, R. E. ; Shi, F. ; Holmes, D. ; Smith, M. R. , III. J. Am Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R., III. J. Am. Chem. Soc. 2003, 125, 7792.

Vorogushin, A. V. ; Huang, X. ;Buchwald, S. L. J. Am. Chem. Soc

Torraca, K. E. ; Huang, X. ; Parrish, C. ; Buchwald, S. L. J. Am. Chem Torraca, K. E.; Huang, X.; Parrish, C.; Buchwald, S. L. J. Am. Chem.Soc. 2001, 123, 10770.

Torraca, K. E. ; Huang, X. ; Parrish, C. ; Buchwald, S. L. J. Am. Chem Torraca, K. E.; Huang, X.; Parrish, C.; Buchwald, S. L. J. Am. Chem.Soc. 2001, 123, 10770.

Liao, Y.; Smith, J.; Fathi, R.; Yang, Z. Org. Lett. 2005, 7, 2707.

Mechanism