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Literature DB >> 29319323

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

Stephanie A Murray¹, Eugenia C M Luc¹, Simon J Meek¹.

Abstract

A practical and broadly applicable catalytic method for the synthesis of (E)-alkenylborons is presented. Reactions are promoted by [Pd(Cl)(η3-C3H5)]2 and proceed by the dehydroboration of cyclic borates. Through the use of epoxides and readily available di-B(pin)-methane (pin = pinacolato), a range of allylic alcohol-containing alkenyl boronates, including those that contain a tertiary alcohol, may be prepared in up to 75% yield and >20:1 E/Z.

Entities: Chemical Disease Gene Species

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Year: 2018 PMID： 29319323 PMCID： PMC5937844 DOI： 10.1021/acs.orglett.7b03853

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

21 in total

1. Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization.

Authors: Nicklas Selander; Benjamin Willy; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2010-06-01 Impact factor: 15.336

Review 2. The remarkable metal-catalysed olefin metathesis reaction.

Authors: Amir H Hoveyda; Adil R Zhugralin
Journal: Nature Date: 2007-11-08 Impact factor: 49.962

3. Efficient synthesis of diborylalkenes from alkenes and diboron by a new PSiP-pincer palladium-catalyzed dehydrogenative borylation.

Authors: Jun Takaya; Naohiro Kirai; Nobuharu Iwasawa
Journal: J Am Chem Soc Date: 2011-08-02 Impact factor: 15.419

4. Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles.

Authors: Yifeng Chen; Justin P Romaire; Timothy R Newhouse
Journal: J Am Chem Soc Date: 2015-04-28 Impact factor: 15.419

5. Applications of 1-alkenyl-1,1-heterobimetallics in the stereoselective synthesis of cyclopropylboronate esters, trisubstituted cyclopropanols and 2,3-disubstituted cyclobutanones.

Authors: Mahmud M Hussain; Hongmei Li; Nusrah Hussain; Mercedes Ureña; Patrick J Carroll; Patrick J Walsh
Journal: J Am Chem Soc Date: 2009-05-13 Impact factor: 15.419

6. 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

7. Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.

Authors: Gary A Molander; Noel M Ellis
Journal: J Org Chem Date: 2008-08-06 Impact factor: 4.354

8. Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide.

Authors: Yifeng Chen; Aneta Turlik; Timothy R Newhouse
Journal: J Am Chem Soc Date: 2016-01-21 Impact factor: 15.419

9. Generation and tandem reactions of 1-alkenyl-1,1-heterobimetallics: practical and versatile reagents for organic synthesis.

Authors: Hongmei Li; Patrick J Carroll; Patrick J Walsh
Journal: J Am Chem Soc Date: 2008-02-27 Impact factor: 15.419

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

1. Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization.

Review 2. The remarkable metal-catalysed olefin metathesis reaction.

3. Efficient synthesis of diborylalkenes from alkenes and diboron by a new PSiP-pincer palladium-catalyzed dehydrogenative borylation.

4. Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles.

5. Applications of 1-alkenyl-1,1-heterobimetallics in the stereoselective synthesis of cyclopropylboronate esters, trisubstituted cyclopropanols and 2,3-disubstituted cyclobutanones.

6. 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.

7. Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.

8. Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide.

9. Generation and tandem reactions of 1-alkenyl-1,1-heterobimetallics: practical and versatile reagents for organic synthesis.

10. Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes.

1. Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.

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

3. Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration.

4. α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

5. Stereo- and Regiocontrolled Methylboration of Terminal Alkynes.

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