ICIQ

Institut Català d'Investigació Química

Training

Seminar

Home / Training / Seminar Programme

Hypervalent Iodine Reagents in the Direct Oxidative Coupling

Dr. Antonchick copia
Jan 30, 2015 | 12:00
Where: ICIQ Auditorium
Lecturer: Dr. Andrey P. Antonchick
University: Max Planck Institute of Molecular Physiology and Technical University of Dortmund (Germany)
More information: Lecturer web page
2015-01-30 12:00:00 2015-01-30 13:00:00 Europe/Paris Hypervalent Iodine Reagents in the Direct Oxidative Coupling ICIQ Auditorium Lecturer: Dr. Andrey P. Antonchick Max Planck Institute of Molecular Physiology and Technical University of Dortmund (Germany)

Abstract

C-H Bonds are ubiquitous in organic compounds and are among the least reactive bonds. Direct and selective methods of alkane functionalization are important and longstanding goals in chemistry. The direct transformation of C-H bonds into new carbon-carbon or carbon-heteroatom bonds is a fundamental challenge in organic chemistry. Direct oxidative cross-coupling methods offer an environmentally benign and economically attractive synthetic strategy. In order to enhance the utility of C-H bond functionalization, the development of methods that proceed at ambient temperature devoid of transition metal catalysts and metal containing oxidants is highly desired.

We developed novel, highly efficient methods for C-N bond formation by intra- and intermolecular C-H bond functionalization.[1,2] Novel C-N bonds were regioselectively formed under mild reaction conditions in the presence of a hypervalent iodine based reagent or using organocatalytic conditions.[1,2] The developed methodology has been extended to unprecedented metal-free cascade reactions and annulations for the synthesis of various heterocycles.[3-5]

Nitrogen-containing heterocycles are abundant in nature and have extensive applications in chemistry and biology. Numerous methods for the de novo synthesis of heterocycles have been described, but their functionalization by cross-dehydrogenative coupling is far less studied. We demonstrated the functionalization of heterocycles with aldehydes and simple alkanes under metal-free conditions.[6,7] The generality of the method was illustrated by the broad reaction scope. Furthermore, the developed method was applied in one-step natural product syntheses from simple compounds and extended to the synthesis of oxindoles under metal free-conditions.[8]

[1] A.P. Antonchick, R. Samanta, K. Kulikov, J. Lategahn, Angew. Chem. Int. Ed. 2011, 50, 8605.

[2] R. Samanta, J.O. Bauer, C. Strohmann, A.P. Antonchick, Org. Lett. 2012, 14, 5518.

[3] R. Samanta, J. Lategahn, A.P. Antonchick, Chem. Commun. 2012, 48, 3194.

[4] S. Manna, A.P. Antonchick, Angew. Chem., Int. Ed. 2014, 53, 7324

[5] K. Matcha, S. Manna, A.P. Antonchick, Angew. Chem., Int. Ed. 2014, 53, 8163

[6] K. Matcha, A.P. Antonchick, Angew. Chem. Int. Ed. 2013, 52, 2082.

[7] A.P. Antonchick, L. Burgmann, Angew. Chem. Int. Ed. 2013, 52, 3267.

[8] K. Matcha, R. Narayan, A.P. Antonchick, Angew. Chem., Int. Ed. 2013, 52, 7985