Literature DB >> 22475226

Synthesis of acyltrifluoroborates.

Aaron M Dumas1, Jeffrey W Bode.   

Abstract

Acylboranes are among the most elusive boron-containing organic functional groups, a fact that has impeded development of new reactions employing them as substrates. A new synthesis of acyltrifluoroborates from benzotriazole (Bt)-based N,O-acetals has been developed. Two other routes provide acyltrifluoroborates containing alcohols, aldehydes, and carbamates. The ketone-like reactivity of the acyltrifluoroborate functional group is demonstrated, and the first X-ray structure of an acyltrifluoroborate is reported.
© 2012 American Chemical Society

Entities:  

Year:  2012        PMID: 22475226     DOI: 10.1021/ol300668m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.

Authors:  Aaron M Dumas; Gary A Molander; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Synthetic fermentation of bioactive non-ribosomal peptides without organisms, enzymes or reagents.

Authors:  Yi-Lin Huang; Jeffrey W Bode
Journal:  Nat Chem       Date:  2014-09-07       Impact factor: 24.427

3.  Helix stability of oligoglycine, oligoalanine, and oligo-β-alanine dodecamers reflected by hydrogen-bond persistence.

Authors:  Chengyu Liu; Jay W Ponder; Garland R Marshall
Journal:  Proteins       Date:  2014-09-20

4.  Metal-free synthesis of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts.

Authors:  Cassandra L Taylor; Yuri Bolshan
Journal:  J Vis Exp       Date:  2015-02-24       Impact factor: 1.355

5.  PEGylation and Dimerization of Expressed Proteins under Near Equimolar Conditions with Potassium 2-Pyridyl Acyltrifluoroborates.

Authors:  Christopher J White; Jeffrey W Bode
Journal:  ACS Cent Sci       Date:  2018-01-05       Impact factor: 14.553

6.  A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons.

Authors:  Shengjia Lin; Lucia Wang; Negin Aminoleslami; Yanting Lao; Chelsea Yagel; Abhishek Sharma
Journal:  Chem Sci       Date:  2019-03-21       Impact factor: 9.825

7.  Copper-Catalyzed Borylation of Acyl Chlorides with an Alkoxy Diboron Reagent: A Facile Route to Acylboron Compounds.

Authors:  Xiaolei Zhang; Alexandra Friedrich; Todd B Marder
Journal:  Chemistry       Date:  2022-06-13       Impact factor: 5.020

8.  Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.

Authors:  Shengjia Lin; Lucia Wang; Abhishek Sharma
Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825

9.  Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs).

Authors:  Anne Schuhmacher; Tomoya Shiro; Sarah J Ryan; Jeffrey W Bode
Journal:  Chem Sci       Date:  2020-03-10       Impact factor: 9.825

10.  Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors:  Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal:  Chem Sci       Date:  2018-05-16       Impact factor: 9.825

  10 in total

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