109674-45-5Relevant academic research and scientific papers
Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation
Deng, Xi,Guo, Jiandong,Su, Weiping,Wang, Xiaotai,Zhang, Xiaofeng
, 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.
Bench-Stable Sulfoxide-Based Boronates: Preparation and Application in a Tandem Suzuki Reaction
?ubiňák, Marek,Eigner, Václav,Tobrman, Tomá?
supporting information, p. 4604 - 4614 (2018/10/31)
A set of novel aromatic and heteroaromatic bench-stable sulfoxide-based boronates was prepared. The structure of the boronates was established by means of X-ray crystallography, and the prepared boronates were successively used in Suzuki cross-coupling reactions under different conditions. We also developed a tandem Suzuki reaction so that a base is generated during the nucleophilic addition of Grignard reagents to 4-bromobenzaldehyde. The formed intermediates were smoothly coupled with the prepared boronates and the boronic acids under external base-free conditions. (Figure presented.).
A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates
Churches, Quentin I.,Hooper, Joel F.,Hutton, Craig A.
, p. 5428 - 5435 (2015/06/16)
We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.
PROCESS FOR THE BORYLATION OF ARENES AND HETEROARYLS
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Page/Page column 72-73, (2012/03/26)
This invention relates to a novel process for the borylation of arenes and heteroaryls. The present invention also provides novel borenium cations, which act as electrophiles for electrophilic substitution on the arene or heteroaryl ring, as well as to methodology for the preparation of these cations.
SYSTEM FOR CONTROLLING THE REACTIVITY OF BORONIC ACIDS
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Page/Page column 23, (2009/02/11)
A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.
Syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes
Mancilla, Teresa,Carrillo, Lourdes,De La Paz Reducindo
, p. 3777 - 3785 (2008/10/09)
The syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes (2 to 6) and their corresponding N-alkylaminodiacetic acids (7 to 10) are reported. All compounds (except 6) were characterized by 1H, 11B (for boron heterocycles), 13C NMR, infrared spectroscopy and mass spectrometry. The 1H NMR spectrum of compound 3 shows that it is a chiral molecule, its structure was determined by homonuclear decoupling experiments, 1H NMR and HETCOR. The study of the intramolecular N → B coordination by dynamic NMR afforded a ΔG? value of 98.4 kJ mol-1 for compound 3. Copyright
