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Literature DB >> 24224801

Transforming Suzuki-Miyaura cross-couplings of MIDA boronates into a green technology: no organic solvents.

Nicholas A Isley¹, Fabrice Gallou, Bruce H Lipshutz.

Abstract

New technology has been developed that enables Suzuki-Miyaura couplings involving widely utilized MIDA boronates to be run in water as the only medium, mainly at room temperature. The protocol is such that no organic solvent is involved at any stage; from the reaction through to product isolation. Hence, using the E factor scale as a measure of greenness, the values for these cross-couplings approach zero.

Entities: Chemical Disease Gene

Mesh：

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Year: 2013 PMID： 24224801 PMCID： PMC4019934 DOI： 10.1021/ja409663q

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

20 in total

1. Regioselective synthesis and slow-release Suzuki-Miyaura cross-coupling of MIDA boronate-functionalized isoxazoles and triazoles.

Authors: Jonathan E Grob; Jill Nunez; Michael A Dechantsreiter; Lawrence G Hamann
Journal: J Org Chem Date: 2011-11-29 Impact factor: 4.354

2. Total synthesis and structural reassignment of (+)-dictyosphaeric acid A: a tandem intramolecular Michael addition/alkene migration approach.

Authors: Alan R Burns; Graeme D McAllister; Stephen E Shanahan; Richard J K Taylor
Journal: Angew Chem Int Ed Engl Date: 2010-07-26 Impact factor: 15.336

3. Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors: Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal: Angew Chem Int Ed Engl Date: 2012-05-09 Impact factor: 15.336

4. Miyaura Borylations of Aryl Bromides in Water at Room Temperature.

Authors: Bruce H Lipshutz; Ralph Moser; Karl R Voigtritter
Journal: Isr J Chem Date: 2010-12-01 Impact factor: 3.333

5. TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors: Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal: J Org Chem Date: 2011-05-09 Impact factor: 4.354

6. Concise total synthesis of (-)-myxalamide A.

Authors: Kazuhiro Fujita; Ryosuke Matsui; Takahiro Suzuki; Susumu Kobayashi
Journal: Angew Chem Int Ed Engl Date: 2012-06-13 Impact factor: 15.336

7. One-pot C-N/C-C cross-coupling of methyliminodiacetic acid boronyl arenes enabled by protective enolization.

Authors: Jonathan E Grob; Michael A Dechantsreiter; Ritesh B Tichkule; Michael K Connolly; Ayako Honda; Ronald C Tomlinson; Lawrence G Hamann
Journal: Org Lett Date: 2012-10-23 Impact factor: 6.005

8. A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

Authors: David M Knapp; Eric P Gillis; Martin D Burke
Journal: J Am Chem Soc Date: 2009-05-27 Impact factor: 15.419

9. Cyclic triolborates: air- and water-stable ate complexes of organoboronic acids.

Authors: Yasunori Yamamoto; Miho Takizawa; Xiao-Qiang Yu; Norio Miyaura
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

10. A general solution for the 2-pyridyl problem.

Authors: Graham R Dick; Eric M Woerly; Martin D Burke
Journal: Angew Chem Int Ed Engl Date: 2012-01-27 Impact factor: 15.336

13 in total

1. HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature.

Authors: Sachin Handa; Martin P Andersson; Fabrice Gallou; John Reilly; Bruce H Lipshutz
Journal: Angew Chem Int Ed Engl Date: 2016-02-29 Impact factor: 15.336

2. Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature.

Authors: Sachin Handa; James C Fennewald; Bruce H Lipshutz
Journal: Angew Chem Int Ed Engl Date: 2014-02-24 Impact factor: 15.336

3. Dehalogenation of Functionalized Alkyl Halides in Water at Room Temperature.

Authors: Nicholas A Isley; Matt S Hageman; Bruce H Lipshutz
Journal: Green Chem Date: 2015 Impact factor: 10.182

Review 4. Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

Authors: Andrew Jordan; Callum G J Hall; Lee R Thorp; Helen F Sneddon
Journal: Chem Rev Date: 2022-02-24 Impact factor: 72.087

5. Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Authors: Bruce H Lipshutz; Subir Ghorai
Journal: Green Chem Date: 2014-08-01 Impact factor: 10.182

6. Nanonickel-catalyzed Suzuki-Miyaura cross-couplings in water.

Authors: Sachin Handa; Eric D Slack; Bruce H Lipshutz
Journal: Angew Chem Int Ed Engl Date: 2015-08-25 Impact factor: 15.336

7. Chemoselective boronic ester synthesis by controlled speciation.

Authors: James W B Fyfe; Ciaran P Seath; Allan J B Watson
Journal: Angew Chem Int Ed Engl Date: 2014-09-29 Impact factor: 15.336

8. C(sp³)-C(sp²) cross-coupling of alkylsilicates with borylated aryl bromides - an iterative platform to alkylated aryl- and heteroaryl boronates.

Authors: Brandon A Vara; Matthieu Jouffroy; Gary A Molander
Journal: Chem Sci Date: 2016-09-09 Impact factor: 9.825

9. Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium.

Authors: Erfei Wang; Mao Chen
Journal: Chem Sci Date: 2019-07-23 Impact factor: 9.825

10. Use of N-methyliminodiacetic acid boronate esters in suzuki-miyaura cross-coupling polymerizations of triarylamine and fluorene monomers.

Authors: Andrew B Foster; Viktor Bagutski; Josue I Ayuso-Carrillo; Martin J Humphries; Michael J Ingleson; Michael L Turner
Journal: J Polym Sci A Polym Chem Date: 2017-07-03 Impact factor: 2.702