Literature DB >> 31012586

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids.

Stefan P A Hinkes1, Christian D P Klein1.   

Abstract

Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.

Entities:  

Year:  2019        PMID: 31012586     DOI: 10.1021/acs.orglett.9b00584

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


  12 in total

1.  Enantioselective catalytic 1,2-boronate rearrangements.

Authors:  Hayden A Sharma; Jake Z Essman; Eric N Jacobsen
Journal:  Science       Date:  2021-11-04       Impact factor: 47.728

2.  "Benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers.

Authors:  Matthew B Minus; Sarah R Moor; Fathima F Pary; L P T Nirmani; Malgorzata Chwatko; Brandon Okeke; Josh E Singleton; Toby L Nelson; Nathaniel A Lynd; Eric V Anslyn
Journal:  Org Lett       Date:  2021-03-30       Impact factor: 6.005

3.  Evaluation of borinic acids as new, fast hydrogen peroxide-responsive triggers.

Authors:  Blaise Gatin-Fraudet; Roxane Ottenwelter; Thomas Le Saux; Stéphanie Norsikian; Mathilde Pucher; Thomas Lombès; Aurélie Baron; Philippe Durand; Gilles Doisneau; Yann Bourdreux; Bogdan I Iorga; Marie Erard; Ludovic Jullien; Dominique Guianvarc'h; Dominique Urban; Boris Vauzeilles
Journal:  Proc Natl Acad Sci U S A       Date:  2021-12-14       Impact factor: 12.779

4.  Programmable nano-reactors for stochastic sensing.

Authors:  Wendong Jia; Chengzhen Hu; Yuqin Wang; Yuming Gu; Guangrui Qian; Xiaoyu Du; Liying Wang; Yao Liu; Jiao Cao; Shanyu Zhang; Shuanghong Yan; Panke Zhang; Jing Ma; Hong-Yuan Chen; Shuo Huang
Journal:  Nat Commun       Date:  2021-10-04       Impact factor: 14.919

Review 5.  Merging the Versatile Functionalities of Boronic Acid with Peptides.

Authors:  Yahong Tan; Junjie Wu; Lulu Song; Mengmeng Zhang; Christopher John Hipolito; Changsheng Wu; Siyuan Wang; Youming Zhang; Yizhen Yin
Journal:  Int J Mol Sci       Date:  2021-11-30       Impact factor: 5.923

6.  ROS-responsive 18β-glycyrrhetic acid-conjugated polymeric nanoparticles mediate neuroprotection in ischemic stroke through HMGB1 inhibition and microglia polarization regulation.

Authors:  Lulu Jin; Zhixin Zhu; Liangjie Hong; Zhefeng Qian; Fang Wang; Zhengwei Mao
Journal:  Bioact Mater       Date:  2022-04-01

7.  Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety.

Authors:  Andrej Šterman; Izidor Sosič; Zdenko Časar
Journal:  Chem Sci       Date:  2022-01-26       Impact factor: 9.825

8.  Facile deprotection of F-BODIPYs using methylboronic acid.

Authors:  Craig D Smith; Alison Thompson
Journal:  RSC Adv       Date:  2020-06-25       Impact factor: 4.036

9.  Diversity-oriented synthesis of peptide-boronic acids by a versatile building-block approach.

Authors:  Stefan P A Hinkes; Severin Kämmerer; Christian D P Klein
Journal:  Chem Sci       Date:  2020-08-21       Impact factor: 9.825

10.  Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates.

Authors:  Julia Altarejos; David Sucunza; Juan J Vaquero; Javier Carreras
Journal:  Org Lett       Date:  2021-07-28       Impact factor: 6.005

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