C−F Bond Activation in Organic Synthesis

Aluminum oxide mediated C–F bond activation in trifluoromethylated arenes

“…[2][3][4][5][6] In this respect, the selective transformation of C-F bond leading to an effective C-C bond formation remains one of the major challenges in modern organic chemistry. [2][3][4][5][6] In particular, the trifluoromethyl group attached to an aromatic ring is surprisingly stable. Despite the presence of three fluorine atoms at the benzylic position examples of the conversion of respective C-F bonds to C-C bond are rare.…”

Palladium-Mediated Organofluorine Chemistry

“…So, the selective cleavage of one or several C-F bonds in those molecules followed by a suitable functionalization is a way to obtain partially fluorinated compounds of high interest. Reviews with an extensive coverage of the subjects of C-F activation, 6,7,[224][225][226] and fluorination 10,227,228 are available in the literature. The purpose of this section is to cover palladium mediated processes in the area.…”

“…A non-comprehensive list of recent reviews is given in references 3-19. 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Some of the challenges for the preparation of organofluorine derivatives lay on the development of suitable fluorine reagents that are not too reactive, as fluorine itself, or too unreactive because in order to give the desired reaction there is the need of the cleavage of a strong E-F bond. Some of the well developed and useful catalytic reactions for non-fluorinated compounds have been applied to the synthesis of fluoroderivatives but, in many cases, the reactions are not as effective as expected or simply do not work.…”

Aromatic C–F Bond Activation by Rare-Earth-Metal Complexes

“…3 Despite the difficulty associated with C-F bond activation, metal mediated C-F bond transformations have been demonstrated and reviewed in the literature, including examples for both early and late transition metals. [15][16][17][18][19][20][21][22] Albeit in most cases C-F bond activation was achieved in a stoichiometric fashion due to the high stability of the corresponding metal fluoride, a common product of metal mediated C-F bond transformations, it is possible to make the reaction catalytic through the use of a fluorine trapper such as a silane or aluminum hydride by taking advantage of the strength of the Si-F and Al-F bonds. [23][24][25][26][27] Scheme 1.…”