Synthesis of N-aryl trifluoromethylarylketoimines by palladium-catalyzed Suzuki coupling reaction of N-aryltrifluoroacetimidoyl chlorides with aryl boronic acids

Highly Efficient Construction of 2‐Fluoroalkyl Quinolines through a Palladium‐Catalyzed 6‐endo‐trig Heck Cyclization Reaction

“…Based on these resultsa nd previous reports, we proposed a classical Heck-typer eactionm echanism (Scheme 4), [10,16] in which the reaction is initiated by oxidative addition of the fluorinated imidoyl chloride (1)t ot he Pd 0 center,t hereby resulting in the formation of intermediate C.T hen, intermediate B is formed through intramolecular insertion of the alkenei nto the CÀPd II bond. Finally,asyn-selective b-hydride elimination of intermediate B generates the 2-fluoroalkyl quinoline product (2) and regenerates the Pd 0 catalyst.…”

“…When the R 1 group was electronically neutral or an electron-donating group, such as an ortho/para-methyl or -methoxy group, excellent yields wereo btained (Table2,e ntries 12-15). However,w hen the R 1 group was an electronwithdrawing group at the ortho/meta/para positions, the corresponding 6-endo-cyclized products were obtained in lower yields ( Table 2, entries [16][17][18][19][20][21]. These results showed that the reactionh ad good tolerance towards halide substituents, which is potentially useful for the further elaboration of morevaluable molecules through cross-coupling reactions.…”

The [3+2] Annulation of CF3-Ketimines by Re Catalysis: Access to CF3-Containing Amino Heterocycles and Polyamides

“…HRMS (ESI) calcd for C14H10F4N + m/z 268.0744 [M+H] + , Found 268.0749. (Li et al, 2010). Following general procedure A, on a 14.5 mmol scale.…”

C−H Activation and Cross‐Coupling of Acyclic Aldonitrone

“…Arylation of double C=N bonds can be achieved in Pd‐catalyzed processes with halogenated substrates, such as chloroimines [14] or N ‐alkoxyimidoyl halides, [15] or even in a metal free reaction of oxime chlorides with arylboronic acids [16] . Transition metal‐catalyzed arylation of H−C=N−X systems involving functionalization of the C(sp 2 )−H bond generally requires additional directing groups (pyridine, pyrimidine, etc.)…”