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Literature DB >> 20107646

Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes.

Abstract

A rhodium-catalyzed dehydrogenative borylation of cyclic alkenes is described. This reaction provides direct access to cyclic 1-alkenylboronic acid pinacol esters, useful intermediates in organic synthesis. Suzuki-Miyaura cross-coupling applications are also presented.

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20107646 PMCID： PMC2825324 DOI： 10.1039/b921387b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

11 in total

1. A stoichiometric aromatic CbondH borylation catalyzed by iridium(i)/2,2'-bipyridine complexes at room temperature.

Authors: Tatsuo Ishiyama; Jun Takagi; John F Hartwig; Norio Miyaura
Journal: Angew Chem Int Ed Engl Date: 2002-08-16 Impact factor: 15.336

2. Selective one-pot carbon-carbon bond formation by catalytic boronation of unactivated cycloalkenes and subsequent coupling.

Authors: Vilhelm J Olsson; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Rhodium catalysed dehydrogenative borylation of alkenes: vinylboronates via C-H activation.

Authors: Ibraheem A I Mkhalid; R Benjamin Coapes; S Natasha Edes; David N Coventry; Fabio E S Souza; Rhodri Ll Thomas; Jonathan J Hall; Si-Wei Bi; Zhenyang Lin; Todd B Marder
Journal: Dalton Trans Date: 2007-12-20 Impact factor: 4.390

4. 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

5. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors: Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal: Science Date: 2001-11-22 Impact factor: 47.728

6. Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes.

Authors: Timothy M Boller; Jaclyn M Murphy; Marko Hapke; Tatsuo Ishiyama; Norio Miyaura; John F Hartwig
Journal: J Am Chem Soc Date: 2005-10-19 Impact factor: 15.419

7. 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

8. Stereoselective synthesis of cis-beta-methyl- and phenyl-substituted alkenylboronates by platinum-catalyzed dehydrogenative borylation.

Authors: Toshimichi Ohmura; Yuta Takasaki; Hideki Furukawa; Michinori Suginome
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

9. Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

Authors: Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura
Journal: J Am Chem Soc Date: 2002-07-10 Impact factor: 15.419

Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes.

1. A stoichiometric aromatic CbondH borylation catalyzed by iridium(i)/2,2'-bipyridine complexes at room temperature.

2. Selective one-pot carbon-carbon bond formation by catalytic boronation of unactivated cycloalkenes and subsequent coupling.

3. Rhodium catalysed dehydrogenative borylation of alkenes: vinylboronates via C-H activation.

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

5. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

6. Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes.

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

8. Stereoselective synthesis of cis-beta-methyl- and phenyl-substituted alkenylboronates by platinum-catalyzed dehydrogenative borylation.

9. Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

10. Vinylic C--H borylation of cyclic vinyl ethers with bis(pinacolato)diboron catalyzed by an Iridium(I)-dtbpy complex.

1. Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration.

2. Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction.

Review 3. Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

4. Palladium-catalyzed hydroboration reaction of unactivated alkynes with bis (pinacolato) diboron in water.

5. Copper-Catalyzed Triboration of Terminal Alkynes Using B₂ pin₂ : Efficient Synthesis of 1,1,2-Triborylalkenes.