Literature DB >> 21192650

Oxidation of organotrifluoroborates via oxone.

Gary A Molander1, Livia N Cavalcanti.   

Abstract

A method for the oxidation of organotrifluoroborates using Oxone was developed. A variety of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates were converted into the corresponding oxidized products in excellent yields. This method proved to be tolerant of a broad range of functional groups, and in secondary alkyl substrates it was demonstrated to be completely stereospecific.

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Year:  2010        PMID： 21192650      PMCID： PMC3025753          DOI： 10.1021/jo102208d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  40 in total

1.  Oxidation of alkyl trifluoroborates: an opportunity for tin-free radical chemistry.

Authors:  Geoffroy Sorin; Rocio Martinez Mallorquin; Yohan Contie; Alexandre Baralle; Max Malacria; Jean-Philippe Goddard; Louis Fensterbank
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

2.  Palladium-catalyzed hydroxylation of aryl halides under ambient conditions.

Authors:  Alexey G Sergeev; Thomas Schulz; Christian Torborg; Anke Spannenberg; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Synthesis of an acyltrifluoroborate and its fusion with azides to form amides.

Authors:  Gary A Molander; Jessica Raushel; Noel M Ellis
Journal:  J Org Chem       Date:  2010-06-18       Impact factor: 4.354

4.  The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

Authors:  Kevin W Anderson; Takashi Ikawa; Rachel E Tundel; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

5.  2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers.

Authors:  Javier Magano; Michael H Chen; Jerry D Clark; Thomas Nussbaumer
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

6.  Protecting-group-free and catalysis-based total synthesis of the ecklonialactones.

Authors:  Volker Hickmann; Manuel Alcarazo; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

7.  Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.

Authors:  Spencer D Dreher; Siang-Ee Lim; Deidre L Sandrock; Gary A Molander
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

8.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

9.  Functionalization of organotrifluoroborates: reductive amination.

Authors:  Gary A Molander; David J Cooper
Journal:  J Org Chem       Date:  2008-04-16       Impact factor: 4.354

10.  Synthesis and crystal structures of lanthanide 4-benzyloxy benzoates: influence of electron-withdrawing and electron-donating groups on luminescent properties.

Authors:  Sarika Sivakumar; M L P Reddy; Alan H Cowley; Kalyan V Vasudevan
Journal:  Dalton Trans       Date:  2009-11-16       Impact factor: 4.390
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  12 in total

1.  Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides.

Authors:  Chen Zhu; Rui Wang; J R Falck
Journal:  Org Lett       Date:  2012-06-26       Impact factor: 6.005

2.  2-Hydroxyphenacyl ester: a new photoremovable protecting group.

Authors:  Bokolombe Pitchou Ngoy; Peter Sebej; Tomáš Solomek; Bum Hee Lim; Tomáš Pastierik; Bong Ser Park; Richard S Givens; Dominik Heger; Petr Klán
Journal:  Photochem Photobiol Sci       Date:  2012-07-06       Impact factor: 3.982

3.  Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2012-04-24       Impact factor: 4.354

4.  Transition-Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives.

Authors:  Chen Zhu; John R Falck
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

5.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

6.  Pd(II)-catalyzed enantioselective C-H activation/C-O bond formation: synthesis of chiral benzofuranones.

Authors:  Xiu-Fen Cheng; Yan Li; Yi-Ming Su; Feng Yin; Jian-Yong Wang; Jie Sheng; Harit U Vora; Xi-Sheng Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-01-14       Impact factor: 15.419

7.  Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2014-05-06       Impact factor: 4.354

8.  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

9.  Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors:  Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419

10.  Site-Selective C-H Oxygenation via Aryl Sulfonium Salts.

Authors:  Ruocheng Sang; Stamatis E Korkis; Wanqi Su; Fei Ye; Pascal S Engl; Florian Berger; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336
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