Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes

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

Presentation transcript:

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes Reporter: Pengfei Yuan Supervisor: Prof. Yong Huang 2016-06-22

Contents 1. Introduction 2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions 3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insight Outlook 5. Acknowledgement

Contents 1. Introduction 2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions 3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insight Outlook 5. Acknowledgement

Copper hydride Source of hydride Source of copper Red solid Air sensitive

Hydroamination

Two possible regiochemical outcomes S. L. Buchwald, Angew. Chem. Int. Ed. 2016, 55, 48.

Contents 1. Introduction 2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions 3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insight Outlook 5. Acknowledgement

Application of copper(I) hydride complexes 1,4-reduction 1,2-reduction high regioselective absolute stereocontrol create SP3 center hydroalkylation hydroamination

The first highly enantioselective CuH chemistry S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473.

Aminating reagent J. S. Johnson, J. Am. Chem. Soc. 2004, 126, 5680.

Contents 1. Introduction 2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions 3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insight Outlook 5. Acknowledgement

CuH-catalyzed racemic hydroamination of styrene M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.

CuH-catalyzed asymmetrical hydroamination of styrene M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.

Proposed mechanism for hydroamination of styrene M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.

Anti-Markovnikov hydroamination of terminal olefin

Hydroamination of oxa- and azabicyclic alkene M. Miura, Org. Lett. 2014, 16,1498.

Enantioselective synthesis of α-aminosilane S. L. Buchwald, Angew. Chem. Int. Ed. 2015, 54, 1638.

Enantioselective hydroamination of 1,1-disubstituted alkene S. L. Buchwald, J. Am. Chem. Soc. 2014, 136, 15913.

CuH-catalyzed hydroamination of alkyne S. L. Buchwald, Nat. Chem. 2015, 7, 38.

Proposed mechanism for hydroamination of alkyne S. L. Buchwald, Nat. Chem. 2015, 7, 38.

Mechanism study for hydroamination of alkyne S. L. Buchwald, Nat. Chem. 2015, 7, 38.

CuH-catalyzed synthesis of chiral secondary amine S. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 9716.

Competition experiments S. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 9716.

Hydroamination of unactivated internal olefin S. L. Buchwald, Science, 2015, 349, 62.

Calculation S. L. Buchwald, Science, 2015, 349, 62.

Contents 1. Introduction 2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions 3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insight Outlook 5. Acknowledgement

Outlook Amines derived from tri- and tetrasubstituted alkenes; Utilize electrophilic aminating agents to transfer aromatic amines or ammonia or its equivalents.

Contents 1. Introduction 2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions 3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insight Outlook and conclusions 5. Acknowledgement

Thanks for your attention! Acknowledgment Prof. Huang Jiean Chen All members here Thanks for your attention!