Iron‐Catalyzed Cross‐Coupling of Alkyl Halides with Alkenyl Grignard Reagents

Abstract

Cheap and safe: An iron‐catalyzed cross‐coupling reaction between alkyl halides and alkenyl Grignard reagents is described. This CC bond coupling reaction is promoted by the cheap and nontoxic FeCl3 and displays good tolerance against various functional groups.

Synthesis of Iron(III) Complex Bearing Tridentate β-Aminoketonato Ligand: Application to Iron-catalyzed Cross-coupling Reaction of Arylmagnesium Bromides with Alkyl Halides

“…These results indicated that the cross-coupling reaction catalyzed by complex 1 could involve a radical mechanism in the reaction of alkyl halide with the iron species. 6b, 15,16 In our system, the slow addition of phenylmagnesium bromide to the reaction mixture is unfavorable for the formation of the cross-coupled product (Table 1). This procedure resulted in increase of the formation of biphenyl, the homocoupled product.…”

Palladium‐catalysed Suzuki cross‐coupling of primary alkylboronic acids with alkenyl halides

“…[39] From 1-bromo-2-methylprop-1-ene (0.135 g, 1 mmol), ndodecylboronic acid (0.428 g, 2 mmol), Pd complex (0.02 mmol) and Cs 2 CO 3 (0.652 g, 2 mmol), 6 was obtained in 63% (0.141 g) yield. 1 (Z)-Pentadec-2-ene (7) [40] From (Z)-1-bromoprop-1-ene (0.121 g, 1 mmol), n-dodecylboronic acid (0.428 g, 2 mmol), Pd complex (0.02 mmol) and Cs 2 CO 3 (0.652 g, 2 mmol), 7 was obtained in 62% (0.130 g) yield.…”

“…1.36-1.16 (m, 12H), 0.88 (t, J = 7.5 Hz, 3H). [39] From 2-bromopropene (0.121 g, 1 mmol), n-dodecylboronic acid (0.428 g, 2 mmol), Pd complex (0.02 mmol) and Cs 2 CO 3 (0.652 g, 2 mmol), 11 was obtained in 64% (0.135 g) yield.…”

Stereoselective Formal Synthesis of (+)-Allokainic Acid <i>via</i> Thiol-Mediated Acyl Radical Cyclization

“…42) Tosylate 13 was treated with lithium bromide to give 16 and the trans-isomer in 55% and 27% yield, respectively (Chart 6). The relative configuration of the products was determined by nOe experiments (see Experimental).…”