Literature DB >> 20485806

Regioselective formation of 1,1-disubstituted allenylsilanes via cross-coupling reactions of 3-tri-n-butylstannyl-1-trimethylsilyl-1-propyne.

David R Williams1, Akshay A Shah.   

Abstract

The regioselective Stille cross-coupling reactions of 3-tri-n-butylstannyl-1-trimethylsilyl-1-propyne demonstrate isomerization following the initial transmetalation step resulting in allenyl palladium intermediates for reductive coupling to yield conjugated 1,1-disubstituted allenylsilanes.

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Year:  2010        PMID： 20485806      PMCID： PMC2924876          DOI： 10.1039/c0cc00679c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

1.  Total synthesis of (+)-amphidinolide K.

Authors:  D R Williams; K G Meyer
Journal:  J Am Chem Soc       Date:  2001-01-31       Impact factor: 15.419

2.  Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors:  Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-06-05       Impact factor: 15.419

3.  Reactivity studies of 3,3-bis(trimethylsilyl)-2-methyl-1-propene in Lewis acid-catalyzed allylation reactions.

Authors:  David R Williams; Angel I Morales-Ramos; Catherine M Williams
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

4.  A new entry to the synthesis of 2,3-disubstituted indoles.

Authors:  Chisato Mukai; Yukie Takahashi
Journal:  Org Lett       Date:  2005-12-22       Impact factor: 6.005

5.  Tuning of regioselectivity in the coupling reaction involving allenic/propargylic palladium species.

Authors:  Shengming Ma; Aibin Zhang
Journal:  J Org Chem       Date:  2002-04-05       Impact factor: 4.354

6.  Palladium pincer complex catalyzed stannyl and silyl transfer to propargylic substrates: synthetic scope and mechanism.

Authors:  Johan Kjellgren; Henrik Sundén; Kálmán J Szabó
Journal:  J Am Chem Soc       Date:  2005-02-16       Impact factor: 15.419

7.  1-alkoxyallene as an effective precursor for regio- and stereocontrolled allylation reactions with aliphatic aldehydes via bis-stannylation.

Authors:  David R Williams; Micheal W Fultz
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

8.  Synthesis of allenes via palladium-catalyzed hydrogen-transfer reactions: propargylic amines as an allenyl anion equivalent.

Authors:  Hiroyuki Nakamura; Takaya Kamakura; Makoto Ishikura; Jean-François Biellmann
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419
  8 in total
  3 in total

1.  A bidirectional S(E)' strategy for 1,5-syn and 1,5-anti stereocontrol toward the synthesis of complex polyols.

Authors:  David R Williams; Christopher D Claeboe; Bo Liang; Nicolas Zorn; Nicholas S C Chow
Journal:  Org Lett       Date:  2012-07-19       Impact factor: 6.005

2.  Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates.

Authors:  Scott E Denmark; Andrea Ambrosi
Journal:  Synlett       Date:  2017-07-12       Impact factor: 2.454

3.  Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes.

Authors:  Zheng-Li Liu; Chao Yang; Qi-Yan Xue; Meng Zhao; Cui-Cui Shan; Yun-He Xu; Teck-Peng Loh
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-04       Impact factor: 15.336
  3 in total

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