Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
2.6.1 Trifluoromethylation

DOI: 10.1055/sos-SD-213-00216

Lishchynskyi, A.; Novák, P.; Grushin, V. V.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20142367.

General Introduction

The trifluoromethyl group (CF3) occupies a special place among other C-1 building blocks in synthetic organic chemistry for at least two reasons. First, trifluoromethylated compounds play an important role as intermediates and building blocks for the preparation of pharmaceuticals, agrochemicals, monomers, and specialty materials (for selected examples, see Scheme 1). Second, in most cases, traditional methods for carbon—alkyl bond formation are not applicable to trifluoromethylation. In particular, trifluoroiodomethane, bromotrifluoromethane, and chlorotrifluoromethane are reluctant to undergo nucleophilic displacement of the heavier halogen. Furthermore, trifluoromethyl derivatives of active metals that are widely used in synthesis (e.g., Mg, Li) are unstable or nonexistent because of facile α-fluoro-elimination reactions leading to metal fluorides and difluorocarbene. Finally, widely used palladium- and nickel-catalyzed cross-coupling reactions are inapplicable to analogous trifluoromethylation processes because of the exceptional strength and inertness of the late-transition-metal–trifluoromethyl bonds. It follows that the development of synthetic methods for the selective trifluoromethylation of various organic molecules is not only important, but also challenging.

Meeeeee eeeeeeeeee eee eeeeeeeeeeee, eeeeeeeeeeeee, eee eeeeeee eeeeeeeeeeeeeeeeeeeee eeee eeee eeeeeeee.[‌8‌] Me eeee eeeeeee, eee eeeee eeee ee ee M—MM8 eeee eeeeeee eeeeeeeee eeee eee eeeeeeee ee eeeeeeeee ee eeeeeeeeee eeeeee, eeee eeeeeeee ee eeeeeeeee eeeee: eeeee, eeeeeeeeeee, eeeeeeeeee, eee eeeeeeeeeee. Me eeeeeeeeeeeeeeeee ee eee eee eeee, eeeeeeeeee-eeeee-eeee eeeeeeeeeeeeeeeeeeee eeeeeeeee eee eeee eeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeee eeeeeeee eeee eee ee eeeeeeeee. Meeeeeeeeeeee eeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeeeeeeee eeeeeeeee[‌8‌] eee eeeeeeeeeeee eeeeeeeeeeeeeeeeeeee eeee eeeeeeeee(eeeeeeeeeeeeeee)eeeeee (Meeeeeeʼe eeeeeee) eee eee eeeeeeeee.[‌8‌,‌8‌] Meee eeeeeeee, eeeeeee eeeeeeeeeeeeeeeeeeee eeeeeee eeee eeeeeeee ee Meeeee.[‌8‌]

Meeeee 8 Meeeeeee ee Meeeeeeeeeeeeee Meeeeeeeeee Meee ee Meeeeeeeeeeeeee eee Meeeeeeeeeeee

References