Copper Hydride-Catalyzed Hydroamination of Alkenes and Alkynes
Study on copper hydride-catalyzed hydroamination of alkenes and alkynes led by Pengfei Yuan under the supervision of Prof. Yong Huang in 2016. The report covers the exploration of copper(I) hydride complexes, hydroxylamine esters, and related reactions, highlighting the scope and mechanistic insights of copper(I) hydride-catalyzed hydroamination. The research provides an outlook on the application of copper(I) hydride complexes in various reactions, demonstrating high regioselectivity and stereocontrol. Noteworthy achievements include the first highly enantioselective CuH chemistry.
Download Presentation
Please find below an Image/Link to download the presentation.
The content on the website is provided AS IS for your information and personal use only. It may not be sold, licensed, or shared on other websites without obtaining consent from the author.If you encounter any issues during the download, it is possible that the publisher has removed the file from their server.
You are allowed to download the files provided on this website for personal or commercial use, subject to the condition that they are used lawfully. All files are the property of their respective owners.
The content on the website is provided AS IS for your information and personal use only. It may not be sold, licensed, or shared on other websites without obtaining consent from the author.
E N D
Presentation Transcript
Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes Reporter: Pengfei Yuan Supervisor: Prof. Yong Huang 2016-06-22 1
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 4. Outlook 5. Acknowledgement 2
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 4. Outlook 5. Acknowledgement 3
Copper hydride Source of hydride Source of copper Red solid Air sensitive 4
Two possible regiochemical outcomes 6 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 4. Outlook 5. Acknowledgement 7
Application of copper(I) hydride complexes 1,4-reduction 1,2-reduction high regioselective absolute stereocontrol create SP3center hydroalkylation hydroamination 8
The first highly enantioselective CuH chemistry 9 S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473.
Aminating reagent J. S. Johnson, J. Am. Chem. Soc. 2004, 126, 5680. 10
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 4. Outlook 5. Acknowledgement 11
CuH-catalyzed racemic hydroamination of styrene 12 M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.
CuH-catalyzed asymmetrical hydroamination of styrene 13 M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.
Proposed mechanism for hydroamination of styrene 14 M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.
Hydroamination of oxa- and azabicyclic alkene M. Miura, Org. Lett. 2014, 16,1498. 16
Enantioselective synthesis of -aminosilane 17 S. L. Buchwald, Angew. Chem. Int. Ed. 2015, 54, 1638.
Enantioselective hydroamination of 1,1-disubstituted alkene 18 S. L. Buchwald, J. Am. Chem. Soc. 2014, 136, 15913.
CuH-catalyzed hydroamination of alkyne 19 S. L. Buchwald, Nat. Chem. 2015, 7, 38.
Proposed mechanism for hydroamination of alkyne 20 S. L. Buchwald, Nat. Chem. 2015, 7, 38.
Mechanism study for hydroamination of alkyne 21 S. L. Buchwald, Nat. Chem. 2015, 7, 38.
CuH-catalyzed synthesis of chiral secondary amine 22 S. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 9716.
Competition experiments 23 S. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 9716.
Hydroamination of unactivated internal olefin 24 S. L. Buchwald, Science, 2015, 349, 62.
Calculation 25 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 4. Outlook 5. Acknowledgement 26
Outlook Amines derived from tri- and tetrasubstituted alkenes; Utilize electrophilic aminating agents to transfer aromatic amines or ammonia or its equivalents. 27
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 4. Outlook and conclusions 5. Acknowledgement 28
Acknowledgment Prof. Huang Jiean Chen All members here Thanks for your attention! 29
