Alkenes and Alkynes 20160622 Reporter Pengfei Yuan Supervisor Prof Yong Huang 2 1 Introduction 2 Study of copperI Hydride complexes h ydroxylamine esters ID: 1037676
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1. 1Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes2016-06-22Reporter: Pengfei YuanSupervisor: Prof. Yong Huang
2. 21. Introduction2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insightOutlook5. AcknowledgementContents
3. 3Contents1. Introduction2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insightOutlook5. Acknowledgement
4. 4Red solidAir sensitiveSource of copperCopper hydride Source of hydride
5. 5 Hydroamination
6. 6Two possible regiochemical outcomes S. L. Buchwald, Angew. Chem. Int. Ed. 2016, 55, 48.
7. 7Contents1. Introduction2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insightOutlook5. Acknowledgement
8. 81,4-reduction1,2-reductionhydroaminationhydroalkylationApplication of copper(I) hydride complexeshigh regioselectiveabsolute stereocontrolcreate SP3 center
9. 9The first highly enantioselective CuH chemistry S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473.
10. 10J. S. Johnson, J. Am. Chem. Soc. 2004, 126, 5680.Aminating reagent
11. 11Contents1. Introduction2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insightOutlook5. Acknowledgement
12. 12M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.CuH-catalyzed racemic hydroamination of styrene
13. 13M. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.CuH-catalyzed asymmetrical hydroamination of styrene
14. 14Proposed mechanism for hydroamination of styreneM. Miura, Angew. Chem. Int. Ed. 2013, 52, 10830.
15. 15Anti-Markovnikov hydroamination of terminal olefin
16. 16M. Miura, Org. Lett. 2014, 16,1498.Hydroamination of oxa- and azabicyclic alkene
17. 17S. L. Buchwald, Angew. Chem. Int. Ed. 2015, 54, 1638.Enantioselective synthesis of α-aminosilane
18. 18Enantioselective hydroamination of 1,1-disubstituted alkeneS. L. Buchwald, J. Am. Chem. Soc. 2014, 136, 15913.
19. 19CuH-catalyzed hydroamination of alkyneS. L. Buchwald, Nat. Chem. 2015, 7, 38.
20. 20S. L. Buchwald, Nat. Chem. 2015, 7, 38.Proposed mechanism for hydroamination of alkyne
21. 21Mechanism study for hydroamination of alkyne S. L. Buchwald, Nat. Chem. 2015, 7, 38.
22. 22CuH-catalyzed synthesis of chiral secondary amineS. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 9716.
23. 23Competition experimentsS. L. Buchwald, J. Am. Chem. Soc. 2015, 137, 9716.
24. 24S. L. Buchwald, Science, 2015, 349, 62.Hydroamination of unactivated internal olefin
25. 25CalculationS. L. Buchwald, Science, 2015, 349, 62.
26. 261. Introduction2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insightOutlook5. AcknowledgementContents
27. 27OutlookAmines derived from tri- and tetrasubstituted alkenes;Utilize electrophilic aminating agents to transfer aromatic amines or ammonia or its equivalents.
28. 28Contents1. Introduction2. Study of copper(I) Hydride complexes, hydroxylamine esters and related reactions3. Copper(I) hydride-catalyzed hydroamination: scope, and mechanistic insightOutlook and conclusions5. Acknowledgement
29. 29Prof. HuangJiean ChenAll members hereThanks for your attention!Acknowledgment