86253-12-5Relevant articles and documents
Template synthesis and structures of apically functionalized iron(II) clathrochelates
Voloshin,Varzatskii,Vorontsov,Antipin,Lebedev,Belov,Palchik
, p. 1552 - 1561 (2003)
Template condensation of three nioxime or dichloroglyoxime molecules with monosubstituted boronic acids on an iron(II) ion matrix afforded apically functionalized tris-nioximate clathrochelates and hexachloride precursors of apically-ribbed functionalized
Practical and Modular Construction of C(sp3)-Rich Alkyl Boron Compounds
Yang, Yangyang,Tsien, Jet,Ben David, Ayala,Hughes, Jonathan M. E.,Merchant, Rohan R.,Qin, Tian
supporting information, p. 471 - 480 (2021/01/13)
Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method is extensively examined through a variety of substrates, including synthesis and late-stage functionalization of scaffolds relevant to medicinal chemistry. The strategic significance of this approach, with alkyl boronic acids as linchpins, is demonstrated through various downstream functionalizations of the alkyl boron compounds. This two-step concurrent cross-coupling approach, resembling formal and flexible alkyl-alkyl couplings, provides a general entry to synthetically challenging high Fsp3-containing drug-like scaffolds.
A General C(sp3)-C(sp3) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids
Merchant, Rohan R.,Lopez, Jovan A.
supporting information, p. 2271 - 2275 (2020/03/13)
A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp3-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.
SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS
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Paragraph 0102-0103; 0110, (2013/03/26)
Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.
Reaction of grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)- aminoborane by a simple hydrolysis
Bailey, Christopher L.,Murphy, Chris L.,Clary, Jacob W.,Eagon, Scott,Gould, Naomi,Singaram, Bakthan
, p. 331 - 341 (2013/08/23)
Diisopropylaminoborane (BH2-N(iPr)2) is prepared by reacting lithium diisopropylaminoborohydride (iPr-LAB) with trimethylsilyl chloride (TMSCl). Aliphatic, aromatic, and heteroaromatic (diisopropylamino) boranes are readily synthesiz
