Literature DB >> 23072212

Regioselective reductive hydration of alkynes to form branched or linear alcohols.

Le Li1, Seth B Herzon.   

Abstract

The regioselective reductive hydration of terminal alkynes using two complementary dual catalytic systems is described. Branched or linear alcohols are obtained in 75-96% yield with ≥25:1 regioselectivity from the same starting materials. The method is compatible with terminal, di-, and trisubstituted alkenes. This reductive hydration constitutes a strategic surrogate to alkene oxyfunctionalization and may be of utility in multistep settings.

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Year:  2012        PMID: 23072212     DOI: 10.1021/ja307145e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes.

Authors:  Le Li; Seth B Herzon
Journal:  Nat Chem       Date:  2013-11-17       Impact factor: 24.427

2.  Separated tandem catalysis: It's about time.

Authors:  Sarah Abou-Shehada; Jonathan M J Williams
Journal:  Nat Chem       Date:  2014-01       Impact factor: 24.427

3.  Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors:  Megan K Armstrong; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-04-03       Impact factor: 15.419

4.  Differential Dihydrofunctionalization: A Dual Catalytic Three-Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.

Authors:  James E Baumann; Gojko Lalic
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-03       Impact factor: 16.823

5.  Stereospecific synthesis of 23-hydroxyundecylprodiginines and analogues and conversion to antimalarial premarineosins via a Rieske oxygenase catalyzed bicyclization.

Authors:  Papireddy Kancharla; Wanli Lu; Shaimaa M Salem; Jane Xu Kelly; Kevin A Reynolds
Journal:  J Org Chem       Date:  2014-11-18       Impact factor: 4.354

6.  Copper-catalysed selective hydroamination reactions of alkynes.

Authors:  Shi-Liang Shi; Stephen L Buchwald
Journal:  Nat Chem       Date:  2014-12-15       Impact factor: 24.427

7.  One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis.

Authors:  Huan Liu; Sensheng Liu; Haifeng Zhou; Qixing Liu; Chunqin Wang
Journal:  RSC Adv       Date:  2018-04-19       Impact factor: 4.036

  7 in total

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