The palladium-catalyzed cross-coupling reactions of trifluoroethyl iodide with aryl and heteroaryl boronic acid esters

Abstract

The cross-coupling reactions of 1,1,1-trifluoro-2-iodoethane with aryl and heteroaryl boronic acid esters have been successfully achieved. The new protocol allows for a convenient introduction of trifluoroethyl groups into a variety of aryl and heteroaryl moieties under mild conditions.

Transition‐Metal‐Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions

“…After the eluent had been concentrated under vacuum, the residue was purified by silica gel plates to give the pure products. The products were characterized by 1 H NMR, 13 C NMR, LC-MS. 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57…”

“…Being energy-efficient and eco-friendly, a transition-metal-free and mild method for synthesizing 3-(trifluoromethyl)imidazo[1,2-a]pyridine derivatives is still highly desirable. As a part of our ongoing efforts on direct CÀH functionalization and fluorine chemistry, [13] we herein report the first transitionmetal-free protocol for direct CÀH trifluoromethylation and perfluoroalkylation of imidazo [ [a] entry oxidant base solvent (mL) yield (%) [ [a] Reaction conditions: 1 a (0.2 mmol), 2 a (0.6 mmol), PhI (OAc) 2 (2.0 equiv. ), base (3.0 equiv.…”

Development of new methods in modern selective organic synthesis: preparation of functionalized molecules with atomic precision

“…Methods of Pd-catalyzed cross-coupling involving boronic acids or pinacolyl boronates and trifluoroethyl iodide were proposed; for this reaction to occur, the presence of a sterically hindered phosphine ligand, either bidentate Xanthphos or monodentate SPhos, is required. 72,73 However, reactions involving 2,2,2-trifluoroethyl organometallic reagents 8, which are prone to b-elimination, are still unknown. Just recently, stable organoboron compounds of this type [8, M = B(OR) 2 ] were obtained but cross-coupling reactions with these reagents have not been studied as yet.…”

Visible-light-mediated trifluoroethylation of 2-isocyanobiaryl with trifluoroethyl iodide: Synthesis of 6-trifluoroethyl-phenanthridines

“…Recently, significant progress has been achieved for the preparation of trifluoroethylated organic compounds is the direct generation of C-CH 2 CF 3 bonds. Transition-metal-catalyzed cross-coupling trifluoroethylation reactions starting from aryl halides [17,18], boronic acids [19,20], alkynes and alkynyl carboxylic acids [21,22] have emerged as a powerful methods for C(sp 2 /sp)-CH 2 CF 3 bond formation. Another frequently used strategy is the utilization of high reactivity of CF 3 CH 2 radical.…”