Literature DB >> 19007135

Formation of pinacol boronate esters via pyridine iodoborane hydroboration.

Andrew G Karatjas1, Edwin Vedejs.   

Abstract

Hydroboration of alkenes with pyridine iodoborane followed by treatment with pinacol/NaOH affords monoalkyl pinacol boronates in moderate to good yield. Dialkylborinic acid derivatives are formed competitively, especially in the case of terminal alkenes. This side reaction can be minimized by using excess of pyridine iodoborane. More hindered alkenes give the best results.

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Year:  2008        PMID： 19007135      PMCID： PMC2765528          DOI： 10.1021/jo8020049

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Hydroboration with pyridine borane at room temperature.

Authors:  Julia M Clay; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

2.  Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases.

Authors:  Stephen J Baker; Tsutomu Akama; Yong-Kang Zhang; Vittorio Sauro; Chetan Pandit; Rajeshwar Singh; Maureen Kully; Jehangir Khan; Jacob J Plattner; Stephen J Benkovic; Ving Lee; Kirk R Maples
Journal:  Bioorg Med Chem Lett       Date:  2006-09-25       Impact factor: 2.823

3.  Di(isopropylprenyl)borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids.

Authors:  Alexey V Kalinin; Stefan Scherer; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-28       Impact factor: 15.336

4.  A mechanistic alternative for the intramolecular hydroboration of homoallylic amine and phosphine borane complexes.

Authors:  Matthew Scheideman; Peter Shapland; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2003-09-03       Impact factor: 15.419
  4 in total
  2 in total

1.  Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective.

Authors:  Timothy S De Vries; Aleksandrs Prokofjevs; Edwin Vedejs
Journal:  Chem Rev       Date:  2012-04-20       Impact factor: 60.622

2.  Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.

Authors:  Aleksandrs Prokofjevs; Anne Boussonnière; Linfeng Li; Hélène Bonin; Emmanuel Lacôte; Dennis P Curran; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419
  2 in total

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