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New reactivities through gold and chiral Brønsted acid catalysis

Séminaire Chimie ED459

Dr. Nitin T. Patil (COS Lab Catalysis and Organic Synthesis Laboratory, IISERB Indian Institute of Science Education and Research Bhopal, India)

Le Jeudi 13 Décembre 2018 à 14h

ENSCM, Amphithéâtre Godechot (campus Balard, 240 av. Émile-Jeanbrau)

Date de début : 2018-12-13 14:00:00

Date de fin : 2018-12-13 15:30:00

Lieu : ENSCM amphi Godechot (campus Balard, 240 av E. Jeanbrau)

Intervenant : Dr. Nitin T. Patil

COS Lab Catalysis and Organic Synthesis Laboratory, IISERB Indian Institute of Science Education and Research Bhopal, India

Research in our laboratory is focused on the development of new reactions employing gold and chiral Brønsted acid catalysis. We are also interested in the development of “Merged Organo/Gold Catalysis” — a technique supposed to be very important for Au(I) catalysis given the difficulties of transferring chiral information from a ligand disposed 180° from the substrate. Our endeavours in these directions have led to (i) Gold(I)-catalyzed hydroaminaloxylation and Petasis-Ferrier rearrangement cascade,[1] (ii) Oxidative intramolecular 1,2-amino-oxygenation of alkynes,[2] (iii) Catalytic enantioselective aza-Piancatelli rearrangement,[3] (iv) Catalytic enantioselective 1,3-alkyl shift in alkyl aryl ethers,[4] (v) Enantioselective hydroamination–hydroarylation of alkynes,[5] and (vi) Addition/cycloisomerization/transfer hydrogenation cascade to access tetrahydroquinolines.[6] This talk will highlight our efforts to address the gaps in the literature and successful realization of the aforementioned reactions.

References

1. A. B. Gade, N. T. Patil, Org. Lett. 2016, 18, 1844.

2. A. C. Shaikh, D. Ranade, P. R. Rajamohanan, P. P. Kulkarni, N. T. Patil, Angew. Chem. Int. Ed. 2017, 56, 757.

3. A. B. Gade, N. T. Patil, Synlett 2017, 28, 1096.

4. A. B. Gade, P. N. Bagle, P. S. Shinde, V. Bhardwaj, S. Banerjee, A. Chande, N. T. Patil, Angew. Chem. Int. Ed. 2018, 57, 5735.

5. V. S. Shinde,; M. V. Mane, K. Vanka, A. Mallick, N. T. Patil, Chem. Eur. J. 2015, 21, 975.

6. N. T. Patil, V. S. Raut, R. B. Tella, Chem. Commun. 2013, 49, 570.

Contact local ICGM : Prof. Jean-Marc Campagne (équipe AM2N)

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