Literature DB >> 22272663

General and practical one-pot synthesis of dihydrobenzosiloles from styrenes.

Alexey Kuznetsov1, Vladimir Gevorgyan.   

Abstract

A one-pot synthesis of dihydrobenzosiloles from styrenes has been developed. The reaction involves the nickel-catalyzed hydrosilylation of styrene with diphenylsilane, followed by the iridium-catalyzed dehydrogenative cyclization. This method is efficient for both electron-rich and -deficient styrenes and exhibits good functional group tolerance, as well as excellent regioselectivity. The forming dihydrobenzosiloles can be efficiently converted into valuable benzosiloles or 2-hydroxyphenethyl alcohols.
© 2012 American Chemical Society

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Year:  2012        PMID: 22272663      PMCID: PMC3376386          DOI: 10.1021/ol203428c

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


  12 in total

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Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

2.  Iridium-catalyzed arene ortho-silylation by formal hydroxyl-directed C-H activation.

Authors:  Eric M Simmons; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

3.  Efficient iridium-catalyzed C-H functionalization/silylation of heteroarenes.

Authors:  Biao Lu; John R Falck
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Intermolecular and intramolecular, platinum-catalyzed, acceptorless dehydrogenative coupling of hydrosilanes with aryl and aliphatic methyl C-H bonds.

Authors:  Naofumi Tsukada; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

5.  Mechanistic analysis of iridium(III) catalyzed direct C-H arylations: a DFT study.

Authors:  Max García-Melchor; Serge I Gorelsky; Tom K Woo
Journal:  Chemistry       Date:  2011-10-27       Impact factor: 5.236

6.  Rhodium-catalyzed synthesis of silafluorene derivatives via cleavage of silicon-hydrogen and carbon-hydrogen bonds.

Authors:  Tomonari Ureshino; Takuya Yoshida; Yoichiro Kuninobu; Kazuhiko Takai
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

7.  Highly efficient B(C(6)F(5))(3)-catalyzed hydrosilylation of olefins.

Authors:  Michael Rubin; Todd Schwier; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

8.  Palladium-catalyzed direct arylation of electron-deficient polyfluoroarenes with arylboronic acids.

Authors:  Ye Wei; Jian Kan; Min Wang; Weiping Su; Maochun Hong
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

9.  Sequential C-Si bond formations from diphenylsilane: application to silanediol peptide isostere precursors.

Authors:  Lone Nielsen; Troels Skrydstrup
Journal:  J Am Chem Soc       Date:  2008-09-04       Impact factor: 15.419

10.  Development of a sila-Friedel-Crafts reaction and its application to the synthesis of dibenzosilole derivatives.

Authors:  Shunsuke Furukawa; Junji Kobayashi; Takayuki Kawashima
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

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  14 in total

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Journal:  Acc Chem Res       Date:  2017-08-03       Impact factor: 22.384

2.  Stereoselective Synthesis of Trisubstituted Vinyl Bromides by Addition of Alkynes to Oxocarbenium Ions.

Authors:  Andrew R Ehle; Melissa G Morris; Bryan D Klebon; Glenn P A Yap; Mary P Watson
Journal:  Synlett       Date:  2015-09-14       Impact factor: 2.454

3.  Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds.

Authors:  Bo Su; John F Hartwig
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

4.  Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.

Authors:  Caleb Karmel; Bijie Li; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-22       Impact factor: 15.419

5.  Fused heteroaromatic dihydrosiloles: synthesis and double-fold modification.

Authors:  Alexey Kuznetsov; Yoshiharu Onishi; Yoshihiro Inamoto; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-04-29       Impact factor: 6.005

6.  Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

Authors:  William B Reid; Jesse R McAtee; Donald A Watson
Journal:  Organometallics       Date:  2019-09-26       Impact factor: 3.876

7.  Pd-catalyzed modifiable silanol-directed aromatic C-H oxygenation.

Authors:  Chunhui Huang; Nugzar Ghavtadze; Benhur Godoi; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2012-07-02       Impact factor: 5.236

8.  Catalytic Reductive ortho-C-H Silylation of Phenols with Traceless, Versatile Acetal Directing Groups and Synthetic Applications of Dioxasilines.

Authors:  Yuanda Hua; Parham Asgari; Thirupataiah Avullala; Junha Jeon
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419

9.  Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C-H oxidation.

Authors:  Nugzar Ghavtadze; Ferdinand S Melkonyan; Anton V Gulevich; Chunhui Huang; Vladimir Gevorgyan
Journal:  Nat Chem       Date:  2014-01-19       Impact factor: 24.427

10.  The dioxasilepanyl group as a versatile organometallic unit: studies on stability, reactivity, and utility.

Authors:  Hayate Saito; Jun Shimokawa; Hideki Yorimitsu
Journal:  Chem Sci       Date:  2021-06-08       Impact factor: 9.825

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