Literature DB >> 22375950

Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

Ping Zhang1, Ian A Roundtree, James P Morken.   

Abstract

Two highly efficient and convenient methods for the synthesis of functionalized and substituted allylic boronates are described. In one procedure, readily available allylic acetates are converted to allylic boronates catalyzed by Ni/PCy(3) or Ni/PPh(3) complexes with high levels of stereoselectivity and in good yields. Alternatively, the borylation can be accomplished with commercially available Pd catalysts [e.g., Pd(2)(dba)(3), PdCl(2), Pd/C], starting with easily accessed allylic halides.

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Year:  2012        PMID: 22375950      PMCID: PMC3322416          DOI: 10.1021/ol3001552

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


  21 in total

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5.  Chiral Brønsted acid-catalyzed allylboration of aldehydes.

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6.  Asymmetric allylboration of cyclic imines and applications to alkaloid synthesis.

Authors:  T Robert Wu; J Michael Chong
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7.  Palladium(0) versus nickel(0) catalysis in selective functional-group-tolerant sp(3)-sp(3) carbon-carbon bond formations.

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8.  Catalytic enantioselective allylboration of ketones.

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9.  Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.

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Review 10.  Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

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  9 in total

1.  Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings.

Authors:  Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2012-05-17       Impact factor: 15.419

2.  Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

Authors:  Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-07-12       Impact factor: 15.419

3.  Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.

Authors:  Farid W van der Mei; Changming Qin; Ryan J Morrison; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2017-06-24       Impact factor: 15.419

Review 4.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

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5.  γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.

Authors:  Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-01       Impact factor: 15.336

6.  Ruthenium-BINAP Catalyzed Alcohol C-H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation.

Authors:  Khoa D Nguyen; Daniel Herkommer; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-15       Impact factor: 15.419

7.  Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

Authors:  Mihai Raducan; Rauful Alam; Kálmán J Szabó
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8.  Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling.

Authors:  Christopher H Schuster; John R Coombs; Zachary A Kasun; James P Morken
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9.  Catalytic Borylative Opening of Propargyl Cyclopropane, Epoxide, Aziridine, and Oxetane Substrates: Ligand Controlled Synthesis of Allenyl Boronates and Alkenyl Diboronates.

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Journal:  Angew Chem Int Ed Engl       Date:  2015-12-11       Impact factor: 15.336

  9 in total

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