A novel transmetallation of arylzinc species into arylboronates from aryl halides in a barbier procedure

Abstract

A variety of functionalized arylboronates are obtained in moderate to excellent yield by a one-step chemical procedure from the corresponding halides and a haloboronic ester via an intermediate arylzinc species.

Miyaura Borylations of Aryl Bromides in Water at Room Temperature

“…Spectral data for the following compounds matched previously reported data: 3 , 8 4 , 9 5 , 10 6 , 8 7 , 8 9 , 8 10 , 6 11 , 8 12 , 6 13 , 11 15 , 10 16 , 10 17 . 6 …”

Pinacol Boronates by Direct Arene Borylation with Borenium Cations

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Aryl boronate esters are essential synthetic building blocks, their ubiquity arising from ease of handling combined with high efficacy in CÀX (X = C, N, O) bond-forming reactions. [1][2][3][4][5][6][7] Recent alternative approaches avoiding haloarenes include: [4+2] cycloadditions, [8] aryl-CH deprotonation, [9,10] diazonium ions, [11] and direct arene borylation with sterically hindered iridium catalysts. [1][2][3][4][5][6][7] Recent alternative approaches avoiding haloarenes include: [4+2] cycloadditions, [8] aryl-CH deprotonation, [9,10] diazonium ions, [11] and direct arene borylation with sterically hindered iridium catalysts.

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“…[1] Aryl boronate esters are commonly synthesized from arenes by a multistep process involving haloarene intermediates and either stoichiometric hard organometallic reagents or metalcatalyzed cross-coupling (e.g., Cu, Ni, Co, or Pd). [1][2][3][4][5][6][7] Recent alternative approaches avoiding haloarenes include: [4+2] cycloadditions, [8] aryl-CH deprotonation, [9,10] diazonium ions, [11] and direct arene borylation with sterically hindered iridium catalysts. [12][13][14] The latter represents a considerable advance, being highly generic and proceeding in one step from the parent aryl CH.…”

Cyclopalladated Ferrocenylimine as Efficient Catalyst for the Syntheses of Arylboronate Esters

“…(Table 3, entry 1) (3ab): [12] White solid; mp 93-94 8C; 98% yield. (Table 3, entry 2) (3ac): [13] (Table 3, entry 11) (3al): [11] Yellow solid; mp 54-55 8C; 66% yield.…”