Literature DB >> 30384597

BF3-Promoted, Carbene-like, C-H Insertion Reactions of Benzynes.

Hang Shen1, Xiao Xiao1, Moriana K Haj1, Patrick H Willoughby1, Thomas R Hoye1.   

Abstract

Boron trifluoride is observed to promote a variety of C-H insertion reactions of benzynes bearing pendant alkyl groups. Computations and various mechanistic studies indicate that BF3 engages the strained π-bond to confer carbene-like character on the adjacent, noncoordinated benzyne carbon. This represents an unprecedented catalytic role for a non-transition metal such as BF3.

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Year:  2018        PMID: 30384597      PMCID: PMC6386166          DOI: 10.1021/jacs.8b10206

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


  18 in total

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Authors:  S M Bachrach; J C Gilbert; D W Laird
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

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Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

3.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 4.  Catalytic carbene insertion into C-H bonds.

Authors:  Michael P Doyle; Richard Duffy; Maxim Ratnikov; Lei Zhou
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  "Two functional groups in one package": using both alkyne π-bonds in cascade transformations.

Authors:  Igor V Alabugin; Brian Gold
Journal:  J Org Chem       Date:  2013-07-17       Impact factor: 4.354

6.  Triplet acetylenes as synthetic equivalents of 1,2-bicarbenes: phantom n,pi state controls reactivity in triplet photocycloaddition.

Authors:  Tarek A Zeidan; Serguei V Kovalenko; Mariappan Manoharan; Ronald J Clark; Ion Ghiviriga; Igor V Alabugin
Journal:  J Am Chem Soc       Date:  2005-03-30       Impact factor: 15.419

7.  Alkane C-H insertion by aryne intermediates with a silver catalyst.

Authors:  Sang Young Yun; Kung-Pern Wang; Nam-Kyu Lee; Phani Mamidipalli; Daesung Lee
Journal:  J Am Chem Soc       Date:  2013-03-14       Impact factor: 15.419

8.  Elucidating the Reactivity of Vicinal Dicarbenoids: From Lewis Adduct Formation to B-C Bond Activation.

Authors:  Hauke Kelch; Stephanie Kachel; Mehmet Ali Celik; Marius Schäfer; Benedikt Wennemann; Krzysztof Radacki; Alex R Petrov; Matthias Tamm; Holger Braunschweig
Journal:  Chemistry       Date:  2016-08-09       Impact factor: 5.236

9.  Reactivity of Arynes for Arene Dearomatization.

Authors:  Rajdip Karmakar; Anh Le; Peipei Xie; Yuanzhi Xia; Daesung Lee
Journal:  Org Lett       Date:  2018-07-02       Impact factor: 6.005

10.  Formation of ruthenium carbenes by gem-hydrogen transfer to internal alkynes: implications for alkyne trans-hydrogenation.

Authors:  Markus Leutzsch; Larry M Wolf; Puneet Gupta; Michael Fuchs; Walter Thiel; Christophe Farès; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-31       Impact factor: 15.336

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  4 in total

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Authors:  Sahil Arora; Dorian S Sneddon; Thomas R Hoye
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2.  De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A.

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Journal:  Org Lett       Date:  2021-09-20       Impact factor: 6.072

Review 3.  Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.

Authors:  Lucas L Fluegel; Thomas R Hoye
Journal:  Chem Rev       Date:  2021-01-25       Impact factor: 60.622

4.  Versatile Dibenzothio[seleno]phenes via Hexadehydro-Diels-Alder Domino Cyclization.

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Journal:  Front Chem       Date:  2019-05-24       Impact factor: 5.221

  4 in total

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