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Literature DB >> 30444946

Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

Mark D Aparece¹, Chenpeng Gao¹, Gabriel J Lovinger¹, James P Morken¹.

Abstract

Organoboron "ate" complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours.

Entities: CellLine Chemical Disease Gene

Keywords: allyl complexes; boron; homogeneous catalysis; palladium

Mesh：

Substances：
Esters
Palladium

Year: 2018 PMID： 30444946 PMCID： PMC6414219 DOI： 10.1002/anie.201811782

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

32 in total

1. Agostic interactions in transition metal compounds.

Authors: Maurice Brookhart; Malcolm L H Green; Gerard Parkin
Journal: Proc Natl Acad Sci U S A Date: 2007-04-18 Impact factor: 11.205

2. Selection of boron reagents for Suzuki-Miyaura coupling.

Authors: Alastair J J Lennox; Guy C Lloyd-Jones
Journal: Chem Soc Rev Date: 2013-10-03 Impact factor: 54.564

3. Regiocontrolled Cu(I)-catalyzed borylation of propargylic-functionalized internal alkynes.

Authors: Abraham L Moure; Ramón Gómez Arrayás; Diego J Cárdenas; Inés Alonso; Juan C Carretero
Journal: J Am Chem Soc Date: 2012-04-18 Impact factor: 15.419

4. Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

Authors: Fang Gao; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2010-08-18 Impact factor: 15.419

5. Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity.

Authors: Hwanjong Jang; Adil R Zhugralin; Yunmi Lee; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2011-04-28 Impact factor: 15.419

6. Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors: Scott N Mlynarski; Alexander S Karns; James P Morken
Journal: J Am Chem Soc Date: 2012-09-24 Impact factor: 15.419

7. 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

8. An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii.

Authors: Yu-Ming Chung; Chien-Kei Wei; Da-Wei Chuang; Mohamed El-Shazly; Chi-Ting Hsieh; Teigo Asai; Yoshiteru Oshima; Tusty-Jiuan Hsieh; Tsong-Long Hwang; Yang-Chang Wu; Fang-Rong Chang
Journal: Bioorg Med Chem Date: 2013-04-13 Impact factor: 3.641

9. Formal regiocontrolled hydroboration of unbiased internal alkynes via borylation/allylic alkylation of terminal alkynes.

Authors: Abraham L Moure; Pablo Mauleón; Ramón Gómez Arrayás; Juan Carlos Carretero
Journal: Org Lett Date: 2013-04-09 Impact factor: 6.005

10. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.

Authors: Weiye Guan; Alicia K Michael; Melissa L McIntosh; Liza Koren-Selfridge; John P Scott; Timothy B Clark
Journal: J Org Chem Date: 2014-07-14 Impact factor: 4.354

7 in total

Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

1. Agostic interactions in transition metal compounds.

2. Selection of boron reagents for Suzuki-Miyaura coupling.

3. Regiocontrolled Cu(I)-catalyzed borylation of propargylic-functionalized internal alkynes.

4. Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

5. Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity.

6. Direct stereospecific amination of alkyl and aryl pinacol boronates.

7. 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.

8. An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii.

9. Formal regiocontrolled hydroboration of unbiased internal alkynes via borylation/allylic alkylation of terminal alkynes.

10. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.

1. Reactions of organoboron compounds enabled by catalyst-promoted metalate shifts.

2. Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

3. Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents.

4. Synthesis of 1,3-Bis-(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2-Migration.

5. Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration.

6. α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.

7. C-Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes.