6113-62-8Relevant articles and documents
Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation
Deng, Xi,Guo, Jiandong,Su, Weiping,Wang, Xiaotai,Zhang, Xiaofeng
supporting information, p. 24510 - 24518 (2021/08/12)
The Ni-catalyzed decarbonylative borylation of (hetero)aryl carboxylic acids with B2cat2 has been achieved without recourse to any additives. This Ni-catalyzed method exhibits a broad substrate scope covering poorly reactive non-ortho-substituted (hetero)aryl carboxylic acids, and tolerates diverse functional groups including some of the groups active to Ni0 catalysts. The key to achieve this decarbonylative borylation reaction is the choice of B2cat2 as a coupling partner that not only acts as a borylating reagent, but also chemoselectively activates aryl carboxylic acids towards oxidative addition of their C(acyl)?O bond to Ni0 catalyst via the formation of acyloxyboron compounds. A combination of experimental and computational studies reveals a detailed plausible mechanism for this reaction system, which involves a hitherto unknown concerted decarbonylation and reductive elimination step that generates the aryl boronic ester product. This mode of boron-promoted carboxylic acid activation is also applicable to other types of reactions.
Visible light-promoted formation of C-B and C-S bonds under metal- A nd photocatalyst-free conditions
Blank, Lena,Fagnoni, Maurizio,Protti, Stefano,Rueping, Magnus
, p. 1243 - 1252 (2019/02/26)
A green, efficient, photoinduced synthesis of arylboronic esters and aryl sulfides has been developed. Bench stable arylazo sulfones were used as radical precursors for a photocatalyst- A nd additive-free carbon-heteroatom bond formation under visible light. The protocols are applicable to a wide range of substrates, providing products in good yields.
Boron trifluoride facilitated transesterification of dioxaborolanes
Kombala, Chathuri J.,Ekanayake, Dulamini I.,Gross, Dustin E.
supporting information, p. 3782 - 3786 (2017/09/09)
The direct transesterification of dioxaborolanes (alkane-1,2-diol based boronate esters) was explored. Using BF3·OEt2, alkane-1,2-diol based mono- and bis-boronate esters (i.e., pinacol and ethylene glycol) have been converted quantitatively to either benzene-1,2-diol or alkane-1,3-diol based boronate esters. In the case of pinacol esters, esterification is facilitated by the accompanying pinacol rearrangement, thus shifting the reaction equilibrium.
