Literature DB >> 25639468

From minutes to years: predicting organotrifluoroborate solvolysis rates.

Zhibo Liu1, Daniel Chao, Ying Li, Richard Ting, Jihyoon Oh, David M Perrin.   

Abstract

Organotrifluoroborates solvolyze in water at rates that vary over five orders of magnitude. The negative logarithm of the solvolytic rate constant, pk(B-F), correlates exceptionally well with the pKa of the analogous carboxylic acid (R(2) = 0.984). This unforeseen correlation may be of predictive value for several applications including Suzuki-Miyaura cross-coupling reactions and the design of (18)F-organotrifluoroborate radioprosthetic groups.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Suzuki-Miyaura cross coupling; organotrifluoroborates; positron emission tomography; solvolysis

Mesh：

Substances：

Year:  2015        PMID： 25639468     DOI： 10.1002/chem.201405829

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  9 in total

1.  One-step (18)F labeling of biomolecules using organotrifluoroborates.

Authors:  Zhibo Liu; Kuo-Shyan Lin; François Bénard; Maral Pourghiasian; Dale O Kiesewetter; David M Perrin; Xiaoyuan Chen
Journal:  Nat Protoc       Date:  2015-08-27       Impact factor: 13.491

2.  [(18)F]-NHC-BF3 adducts as water stable radio-prosthetic groups for PET imaging.

Authors:  Kantapat Chansaenpak; Mengzhe Wang; Zhanhong Wu; Rehmat Zaman; Zibo Li; François P Gabbaï
Journal:  Chem Commun (Camb)       Date:  2015-08-11       Impact factor: 6.222

3.  18F-Positron Emitting/Trimethine Cyanine-Fluorescent Contrast for Image-Guided Prostate Cancer Management.

Authors:  Harikrishna Kommidi; Hua Guo; Fuad Nurili; Yogindra Vedvyas; Moonsoo M Jin; Timothy D McClure; Behfar Ehdaie; Haluk B Sayman; Oguz Akin; Omer Aras; Richard Ting
Journal:  J Med Chem       Date:  2018-04-20       Impact factor: 7.446

4.  18F-Radiolabeled Panobinostat Allows for Positron Emission Tomography Guided Delivery of a Histone Deacetylase Inhibitor.

Authors:  Harikrishna Kommidi; Umberto Tosi; Uday B Maachani; Hua Guo; Christopher S Marnell; Benedict Law; Mark M Souweidane; Richard Ting
Journal:  ACS Med Chem Lett       Date:  2018-01-17       Impact factor: 4.345

5.  A Murine Model for Quantitative, Real-Time Evaluation of Convection-Enhanced Delivery (RT-CED) Using an 18[F]-Positron Emitting, Fluorescent Derivative of Dasatinib.

Authors:  Melinda Wang; Harikrishna Kommidi; Umberto Tosi; Hua Guo; Zhiping Zhou; Melanie E Schweitzer; Linda Y Wu; Ranjodh Singh; Shengqi Hou; Benedict Law; Richard Ting; Mark M Souweidane
Journal:  Mol Cancer Ther       Date:  2017-10-04       Impact factor: 6.261

6.  An [18F]-Positron-Emitting, Fluorescent, Cerebrospinal Fluid Probe for Imaging Damage to the Brain and Spine.

Authors:  Harikrishna Kommidi; Hua Guo; Nandi Chen; Dohyun Kim; Bin He; Amy P Wu; Omer Aras; Richard Ting
Journal:  Theranostics       Date:  2017-06-15       Impact factor: 11.556

7.  Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles.

Authors:  Anton Yu Shabalin; Nicolay Yu Adonin; Vadim V Bardin
Journal:  Beilstein J Org Chem       Date:  2017-04-12       Impact factor: 2.883

Review 8.  Reaction of [18F]Fluoride at Heteroatoms and Metals for Imaging of Peptides and Proteins by Positron Emission Tomography.

Authors:  Kymberley R Scroggie; Michael V Perkins; Justin M Chalker
Journal:  Front Chem       Date:  2021-06-23       Impact factor: 5.221

9.  Boramino acid as a marker for amino acid transporters.

Authors:  Zhibo Liu; Haojun Chen; Kai Chen; Yihan Shao; Dale O Kiesewetter; Gang Niu; Xiaoyuan Chen
Journal:  Sci Adv       Date:  2015-09-11       Impact factor: 14.136
  9 in total

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