CAS: 6783-05-7; Trans-2-Phenylvinylboronic Acid

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📜[(Z)-2-溴乙烯基]苯置于tris(Dibenzylideneacetone)Dipalladium(0) Chloroform Complex,Diisopropopylaminoborane,三乙胺,三苯基膦,甲醇体系中,用 四氢呋喃 作为反应溶剂,化学反应 12.0H,以51%的收率获得产物反式-Beta-苯乙烯硼酸
参考文献:Lithium Aminoborohydrides 17. Palladium Catalyzed Borylation Of Aryl Iodides,Bromides,And Triflates With Diisopropylaminoborane Prepared From Lithium Diisopropylaminoborohydride
标题:Lithium Aminoborohydrides 17. Palladium Catalyzed Borylation Of Aryl Iodides,Bromides,And Triflates With Diisopropylaminoborane Prepared From Lithium Diisopropylaminoborohydride
摘要:The Alcaraz-Vaultier Borylation Of Aryl Halides And Triflates Is Reported Utilizing Diisopropylaminoborane (Bh2N(Pr-I)(2)) Prepared From The Corresponding Lithium Aminoborohydride (Lab Reagent). Bh2N(Pr-I)(2) Prepared By Reacting Lithium Diisopropylaminoborohydride With Trimethylsilyl Chloride,Provided The Most Consistent Isolated Yields From This Reaction. Catalytic Amounts Of Palladium Dichloride Produced The Highest Yields From Aryl Iodides,While Catalytic Tris(Dibenzylideneacetone)Dipalladium(Chloroform) Provided The Best Yields For Aryl Bromides And Triflates. This Route To Boronic Acids Is Mild Enough To Tolerate Various Functionalities And For The First Time Employs Aryl Triflates As Substrates For The Alcaraz-Vaultier Borylation. In Addition,It Was Found That Both Boronic Acid And Ester Compounds Could Be Isolated From The Reaction Mixture Utilizing Simple Work-Up Procedures. Treatment Of The Reaction Intermediate With An Acid/base Work-Up Provided The Corresponding Boronic Acid,While Treating The Same Intermediate With A Diol,Such As Neopentyl Glycol,Afforded The Corresponding Boronic Ester. (C) 2010 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Tet.2010.11.065

专利信息

专利号:US-9388131-B2
优先权日:2011-04-27
标题:Automated synthesis of small molecules using chiral, non-racemic boronates
发明人：BURKE MARTIN D; LI JUNQI; GILLIS ERIC P
权利人:UNIV ILLINOIS
摘要:Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.

专利号:US-6960654-B2
优先权日:2002-06-11
标题 :Method of forming glycosidic bonds from thioglycosides using an N,N-dialkylsulfinamide
发明人：CRICH DAVID C; SMITH MARK
权利人:UNIV ILLINOIS
摘要:A method of forming a glycosidic bond utilizing an activated thioglycoside is disclosed. The thioglycoside is activated by an N,N-dialkylsulfinamide and trifluoromethanesulfonic anhydride. The method allows the facile synthesis of disaccharides, oligosacchraides, and polysaccharides in solution or on a polymer support.

专利号:US-9670234-B2
优先权日:2014-07-10
标题 :Metal-catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2-substituted-4-oxy-cyclopent-2-en-1-ones yielding prostaglandins and prostaglandin analogs
发明人：HENSCHKE JULIAN PAUL; WU PING-YU; WU HSYUEH-LIANG; WEN WEN-HSIEN
权利人:SCINOPHARM TAIWAN LTD
摘要:This invention provides a novel method for the preparation of 2,3-disubstituted -4-oxy-cyclopentan1-one compounds that are useful for the synthesis of prostaglandins and prostaglandin analogs of industrial relevance. The method comprises the metal-catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2-substituted -4-oxy-cyclopent-2-en-1-ones. This method relies on the use of less toxic, easily-handled reagents, and can be performed under milder conditions than offered by some conventional methods, affording 2,3-disubstituted-4-oxy-cyclopentan-1-one compounds enantio- and diastereoselectively, which are precursors to the said prostaglandin and prostaglandin analogs, in high yield.

专利号:US-7247701-B2
优先权日:2002-04-01
标题:Amino amides, peptides and peptidomimetics
发明人：PETASIS NICOS A; YAO XIN
权利人:UNIV SOUTHERN CALIFORNIA
摘要:Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.

专利号:US-2019315676-A1
优先权日:2011-04-27
标 题 :Automated synthesis of small molecules using chiral, non-racemic boronates

专利号:US-11767302-B2
优先权日:2020-10-01
标题 :Reagents and methods for tetrazine synthesis
发明人：FOX JOSEPH M; LAMBERT WILLIAM; FANG YINZHI; AM ENDE CHRISTOPHER WILLIAM; MAHAPATRA SUBHAM; XIE YIXIN; WANG CHUANQI
权利人:UNIV DELAWARE
摘要:Disclosed herein are mono- and di-substituted tetrazines and methods of their preparation and converting an oxetanyl ester to a thio-substituted tetrazine, which is then converted to a mono-substituted tetrazine, a di-substituted tetrazine, or a vinylether disubstituted tetrazine.