Jurriën Collet
Jurriën ColletPhD Student
 06/2015 – present
Room:  O|2-4W31
Lab:  O|2-4W19
Phone:  +31 20 59 87477
E-mail:  j.w.collet@vu.nl

Lord of the Rings: Catalytic Isocyanide Insertion as a Platform for Cascade Reactions toward Complex and Diverse heterocycles

Palladium-catalyzed CO-insertive cross-coupling reactions have been undoubtedly beneficial to the industrial-scale synthesis of a myriad of valuable chemical intermediates.[1] In terms of step-economy, overall waste-production and atom-economy, carbonylative cross-coupling has proven to be a valuable synthetic tool in the synthesis of nearly all carbonyl-containing compound classes. The isoelectronic properties of isocyanides and carbon monoxide have long been known. However, the implementation of isocyanide insertive (imidoylative) palladium-catalyzed cross coupling reactions has only recently taken up interest.[2]

GA Jurrien

The main advantage point of imidoylative cross-coupling reactions is the addition of a diversity point on the isocyanide-derived nitrogen atom. This diversity point leads to increased complexity in the final product, but can also be applied towards further derivatization of the coupling product in a cascade manner. We attempt to facilitate multi-bond-forming transformations (MBFTs) by isocyanide insertion/ intramolecular cyclization cascades, employing the isocyanide substituent as a reactive handle. These cascade sequences are capable of delivering highly complex nitrogenous heterocycles without intermediate isolation and purification.

[1] J. J. Brunet and R. Chauvin, Chem. Soc. Rev., 1995, 24, 89-95.
[2] a) T. Vlaar, E. Ruijter, B. U. W. Maes and R. V. A. Orru, Angew. Chem. Int. Ed., 2013, 52, 7084-7097; b) G. Van Baelen, S. Kuijer, L. Rýček, S. Sergeyev, E. Janssen, F. J. J. de Kanter, B. U. W. Maes, E. Ruijter and R. V. A. Orru, Chem. Eur. J., 2011, 17, 15039-15044.