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Literature DB >> 24761030

Miyaura Borylations of Aryl Bromides in Water at Room Temperature.

Bruce H Lipshutz¹, Ralph Moser¹, Karl R Voigtritter¹.

Abstract

New technology for palladium-catalyzed cross-couplings between B2pin2 and aryl bromides leading to arylboronates is described. Micellar catalysis serves to enable borylations to take place in water as the only medium at ambient temperatures.

Entities: CellLine Chemical Disease Gene

Keywords: borylation; cross-coupling; green chemistry; micellar catalysis

Year: 2010 PMID： 24761030 PMCID： PMC3994125 DOI： 10.1002/ijch.201000045

Source DB: PubMed Journal: Isr J Chem ISSN： 0021-2148 Impact factor: 3.333

13 in total

1. Reactions in micellar systems.

Authors: Torsten Dwars; Eckhard Paetzold; Günther Oehme
Journal: Angew Chem Int Ed Engl Date: 2005-11-11 Impact factor: 15.336

2. "On water": unique reactivity of organic compounds in aqueous suspension.

Authors: Sridhar Narayan; John Muldoon; M G Finn; Valery V Fokin; Hartmuth C Kolb; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2005-05-20 Impact factor: 15.336

3. Palladium-catalyzed borylation of aryl chlorides: scope, applications, and computational studies.

Authors: Kelvin L Billingsley; Timothy E Barder; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Single organic microtwist with tunable pitch.

Authors: Hai-Bo Chen; Yan Zhou; Jie Yin; Jing Yan; Yuguo Ma; Lei Wang; Yong Cao; Jian Wang; Jian Pei
Journal: Langmuir Date: 2009-05-19 Impact factor: 3.882

5. Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors: K C Nicolaou; Paul G Bulger; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

6. Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Authors: Tatsuo Ishiyama; Jun Takagi; Kousaku Ishida; Norio Miyaura; Natia R Anastasi; John F Hartwig
Journal: J Am Chem Soc Date: 2002-01-23 Impact factor: 15.419

7. Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

Authors: Tatsuo Ishiyama; Norio Miyaura
Journal: Chem Rec Date: 2004 Impact factor: 6.771

8. A novel transmetallation of arylzinc species into arylboronates from aryl halides in a barbier procedure.

Authors: Stéphanie Claudel; Corinne Gosmini; Jean Marc Paris; Jacques Périchon
Journal: Chem Commun (Camb) Date: 2007-06-26 Impact factor: 6.222

9. Cross-coupling reactions of aryl and vinyl chlorides catalyzed by a palladium complex derived from an air-stable H-phosphonate.

Authors: Lutz Ackermann; Christian J Gschrei; Andreas Althammer; Melanie Riederer
Journal: Chem Commun (Camb) Date: 2006-02-21 Impact factor: 6.222

5. Design, synthesis and insecticidal activity of novel analogues of flubendiamide containing alkoxyhexafluoroisopropyl groups.

Authors: Xianghu Zhao; Sixue Xu; Chuan Liu; Jingjing He; Chunmei Li; Yupian Deng; Song Cao
Journal: RSC Adv Date: 2020-09-17 Impact factor: 4.036

5 in total

Miyaura Borylations of Aryl Bromides in Water at Room Temperature.

1. Reactions in micellar systems.

2. "On water": unique reactivity of organic compounds in aqueous suspension.

3. Palladium-catalyzed borylation of aryl chlorides: scope, applications, and computational studies.

4. Single organic microtwist with tunable pitch.

5. Palladium-catalyzed cross-coupling reactions in total synthesis.

6. Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

7. Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

8. A novel transmetallation of arylzinc species into arylboronates from aryl halides in a barbier procedure.

9. Cross-coupling reactions of aryl and vinyl chlorides catalyzed by a palladium complex derived from an air-stable H-phosphonate.

10. Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis.

1. "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

2. "Nok": a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature.

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

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

5. Design, synthesis and insecticidal activity of novel analogues of flubendiamide containing alkoxyhexafluoroisopropyl groups.