Literature DB >> 27443890

Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α-Boryl Ketones.

Wen-Xin Lv1, Yao-Fu Zeng1, Qingjiang Li1,2, Yunyun Chen1, Dong-Hang Tan1, Ling Yang1, Honggen Wang3.   

Abstract

The synthesis of halogenated and trifluoromethylated α-boryl ketones via a one-pot oxidative difunctionalization of alkenyl MIDA boronates is reported. These novel densely functionalized organoborons bearing synthetically and functionally valuable carbonyl, halogen/CF3 and boronate moieties within the same molecule are synthetically challenging for the chemist, but have great synthetic potential, as demonstrated by their applications in a straightforward synthesis of borylated furans. The generality of this reaction was extensively investigated. This reaction is attractive since the starting materials, alkenyl MIDA boronates, are easily accessible.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; halogenation; organoboron; oxidation; trifluoromethylation

Year:  2016        PMID: 27443890     DOI: 10.1002/anie.201604898

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  7 in total

Review 1.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

2.  Toward Generalization of Iterative Small Molecule Synthesis.

Authors:  Jonathan W Lehmann; Daniel J Blair; Martin D Burke
Journal:  Nat Rev Chem       Date:  2018-03-07       Impact factor: 34.035

3.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

Authors:  Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

4.  Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.

Authors:  Yahui Wang; Adam Noble; Christopher Sandford; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-18       Impact factor: 15.336

5.  Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.

Authors:  Shi-Chao Ren; Feng-Lian Zhang; Ai-Qing Xu; Yinuo Yang; Min Zheng; Xiaoguo Zhou; Yao Fu; Yi-Feng Wang
Journal:  Nat Commun       Date:  2019-04-29       Impact factor: 14.919

6.  Hypervalent iodine-mediated β-difluoroalkylboron synthesis via an unusual 1,2-hydrogen shift enabled by boron substitution.

Authors:  Wen-Xin Lv; Yin Li; Yuan-Hong Cai; Dong-Hang Tan; Zhan Li; Ji-Lin Li; Qingjiang Li; Honggen Wang
Journal:  Chem Sci       Date:  2022-02-11       Impact factor: 9.825

Review 7.  Recent Advances in the Construction of Fluorinated Organoboron Compounds.

Authors:  Xingxing Ma; Zhijie Kuang; Qiuling Song
Journal:  JACS Au       Date:  2021-12-30
  7 in total

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