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Literature DB >> 23594305

Synthesis and minisci reactions of organotrifluoroborato building blocks.

Marc Presset¹, Nicolas Fleury-Brégeot, Daniel Oehlrich, Frederik Rombouts, Gary A Molander.

Abstract

Copper-catalyzed borylation of a variety of organic halides with bis(pinacolato)diboron allows the preparation of diverse potassium organotrifluoroborates. The reactions are mild and general, providing access to a variety of interesting, boron-containing building blocks, including those containing piperidine, pyrrole, azetidine, tetrahydropyran, and oxetane substructures. Representative Minisci reactions are reported for select examples.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2013 PMID： 23594305 PMCID： PMC3678362 DOI： 10.1021/jo4005519

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

25 in total

1. Palladium-catalyzed borylation of primary alkyl bromides.

Authors: Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal: J Org Chem Date: 2012-07-23 Impact factor: 4.354

Review 2. Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors: Sylvain Darses; Jean-Pierre Genet
Journal: Chem Rev Date: 2007-12-21 Impact factor: 60.622

3. Synthesis and structural analysis of a new class of azaspiro[3.3]heptanes as building blocks for medicinal chemistry.

Authors: Johannes A Burkhard; Carine Guérot; Henner Knust; Mark Rogers-Evans; Erick M Carreira
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

4. Copper(I)-catalyzed boryl substitution of unactivated alkyl halides.

Authors: Hajime Ito; Koji Kubota
Journal: Org Lett Date: 2012-01-19 Impact factor: 6.005

5. An opportunity for Mg-catalyzed Grignard-type reactions: direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium.

Authors: Christine Pintaric; Sandra Olivero; Yves Gimbert; Pierre Y Chavant; Elisabet Duñach
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

6. Practical radical cyclizations with arylboronic acids and trifluoroborates.

Authors: Jonathan W Lockner; Darryl D Dixon; Rune Risgaard; Phil S Baran
Journal: Org Lett Date: 2011-09-16 Impact factor: 6.005

7. Nickel-catalyzed reductive cross-coupling of unactivated alkyl halides.

Authors: Xiaolong Yu; Tao Yang; Shulin Wang; Hailiang Xu; Hegui Gong
Journal: Org Lett Date: 2011-03-24 Impact factor: 6.005

8. Escape from flatland: increasing saturation as an approach to improving clinical success.

Authors: Frank Lovering; Jack Bikker; Christine Humblet
Journal: J Med Chem Date: 2009-11-12 Impact factor: 7.446

9. Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

Authors: Michael G Organ; Mirvat Abdel-Hadi; Stephanie Avola; Igor Dubovyk; Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Mahmoud Sayah; Cory Valente
Journal: Chemistry Date: 2008 Impact factor: 5.236

10. Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

Authors: Nicolas Fleury-Brégeot; Marc Presset; Floriane Beaumard; Virginie Colombel; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: J Org Chem Date: 2012-11-06 Impact factor: 4.354

17 in total

1. Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles.

Authors: Alexandra C Sun; Edward J McClain; Joel W Beatty; Corey R J Stephenson
Journal: Org Lett Date: 2018-06-01 Impact factor: 6.005

2. Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates.

Authors: Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: J Org Chem Date: 2013-11-19 Impact factor: 4.354

3. Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors: Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal: J Am Chem Soc Date: 2013-07-30 Impact factor: 15.419

Synthesis and minisci reactions of organotrifluoroborato building blocks.

1. Palladium-catalyzed borylation of primary alkyl bromides.

Review 2. Potassium organotrifluoroborates: new perspectives in organic synthesis.

3. Synthesis and structural analysis of a new class of azaspiro[3.3]heptanes as building blocks for medicinal chemistry.

4. Copper(I)-catalyzed boryl substitution of unactivated alkyl halides.

5. An opportunity for Mg-catalyzed Grignard-type reactions: direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium.

6. Practical radical cyclizations with arylboronic acids and trifluoroborates.

7. Nickel-catalyzed reductive cross-coupling of unactivated alkyl halides.

8. Escape from flatland: increasing saturation as an approach to improving clinical success.

9. Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

10. Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

1. Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles.

2. Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates.

3. Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

4. Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.

5. Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

6. Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

7. Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

Review 8. Radicals: Reactive Intermediates with Translational Potential.

9. Direct Assembly of Prenylated Heteroarenes through a Cascade Minisci Reaction/Dehydration Sequence.

10. Practical and Regioselective Synthesis of C-4-Alkylated Pyridines.