VIP Event Grushin

News 13.09.2016

abcr invites fluor chemistry experts for a VIP event with speaker Dr. Vladimir Grushin

On the beautiful sunny day of September 13, 2016, abcr GmbH, Karlsruhe, was pleased to welcome a group of its customers and collaborators from both industry and academia for a special event, an invited seminar by Dr. Vladimir Grushin of K&G Technologies LLC, WY, USA.  In his talk 'Direct Cupration of Fluoroform: From Waste to High-Value Trifluoromethylated Compounds', Vladimir Grushin shared his results on the development of novel methods to efficiently trifluoromethylate a variety of substrates in the most economical way.

Following active exchange of ideas and discussions during the reception and after the seminar, the participants enjoyed a tour of the abcr facilities given by Dr. Jan Schuricht, abcr Managing Director. The tour included a visit to the storage rooms and detailed explanations of safety measurements taken while handling customers' orders.

The attendees and the abcr team unanimously concurred in the opinion that the event was highly successful, featuring many useful discussions of cooperation between the groups in the future.


New access to High-Value Trifluoromethylated Compounds

Direct Cupration of Fluoroform
Speaker – Vladimir Grushin

 

Direct Cupration of Fluoroform:
From Waste to High-Value Trifluoromethylated Compounds

Vladimir V. Grushin
K&G Technologies LLC, WY, USA

Trifluoromethylated building blocks and intermediates are in increasingly high demand for the synthesis of agrochemicals, pharmaceuticals, and specialty materials.1 Readily available fluoroform (CHF3), a side-product of the fluoropolymer and fluorochemicals industries and a potent greenhouse gas, is by far the best CF3 source for trifluoromethylation reactions.1,2However, chemoselective activation of highly inert fluoroform is exceedingly challenging. In recent years, a novel promising methodology has emerged for CHF3 activation with transition metals. This presentation will focus on our contributions to the area (Scheme below), including (i) the first reactions of direct cupration1-5 and palladation6 of fluoroform to furnish CuCF3 and PdCF3 complexes in nearly quantitative yield; (ii) the development of new, lowcost, highly efficient, and selective fluoroalkylation methods with our CuRf (Rf = CF3, C2F5) reagents prepared from CHF3 and C2F5H;7-14 and (iii) remarkable mechanisms of the cupration of CHF35 and aromatic trifluoromethylation reactions with CuCF3.15,16

Keywords: Fluoroform · Trifluoromethylation · Pentafluoroethylation · Reaction Mechanisms

1Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011111, 4475. 2Grushin, V. V. Chim. Oggi 201432, 81. 3Zanardi, A; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011133, 20901. 4Mazloomi, Z.; Bansode, A.; Benavente, P.; Lishchynskyi, A.; Urakawa, A.; Grushin, V. V. Org. Process Res. Dev. 201418, 1020. 5Konovalov, A. I.; Benet-Buchholz, J.; Martin, E.; Grushin, V. V. Angew. Chem. Int. Ed. 201352, 11637. 6Takemoto, S.; Grushin, V. V. J. Am. Chem. Soc. 2013135, 16837. 7Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem. Int. Ed. 201251, 7767. 8Novák, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012134, 16167. 9Lishchynskyi, A.; Novikov, M. A.; Martin, E.; Escudero-Adán, E. C.; Novák, P.; Grushin, V. V. J. Org. Chem. 201378, 11126. 10Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc.2013135, 12584. 11Lishchynskyi, A.; Berthon, G.; Grushin, V. V. Chem. Commun. 201450, 10237. 12Lishchynskyi, A.; Mazloomi, Z.; Grushin, V. V. Synlett 201526, 45. 13Romine, A. M.; Nebra, N.; Konovalov, A. I.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. Angew. Chem., Int. Ed. 201554, 2745. 14Panferova, L. I.; Miloserdov, F. M.; Lishchynskyi, A.; Martínez Belmonte, M.; Benet-Buchholz, J.; Grushin, V. V. Angew. Chem., Int. Ed. 201554, 5218. 15Konovalov, A. I.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2014136, 13410. 16Nebra, N.; Grushin, V. V. J. Am. Chem. Soc. 2014136, 16998.