Site-Selective Functionalization of C(sp<sup>3</sup>) Vicinal Boronic Esters
نویسندگان
چکیده
Selective functionalization of the C–B bond in 1,2-bis(boronate) esters has emerged as a powerful tool to prepare 1,2-difunctionalized compounds with stereocontrol. Suzuki cross-coupling, oxidation, amination, and homologation reactions serve platforms wide variety from common intermediate. The exquisite selectivity offered their easy preparation feedstock material using myriad catalytic transformations make them attractive building blocks for complex molecules. In this Perspective, we summarize examples selective vicinal bis(boronates), attending nature functionalization.
منابع مشابه
Stereodivergent Olefination of Enantioenriched Boronic Esters
A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process ...
متن کاملA borylative cyclisation towards indole boronic esters.
2-Alkynylaniline borylative cyclisations provide a direct means to access indole 3-boronic esters from simple precursors. The Pd-catalysed cyclisation can be merged with cross-coupling processes in the same reaction vessel, moreover, the products can be exploited in C-N bond forming reactions.
متن کاملHighly selective allylborations of aldehydes using α,α-disubstituted allylic pinacol boronic esters.
α,α-Disubstituted allylic pinacol boronic esters undergo highly selective allylborations of aldehydes to give tetrasubstituted homoallylic alcohols with exceptional levels of anti-Z-selectivity (>20:1). The scope of the reaction includes both acyclic and cyclic allylic boronic esters which lead to acyclic and exocyclic tetrasubstituted homoallylic alcohols. The use of β-borylated allylic boroni...
متن کاملSelective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Here...
متن کاملVisible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an α-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α-amino, α-oxy, ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2022
ISSN: ['2155-5435']
DOI: https://doi.org/10.1021/acscatal.2c02857