Literature DB >> 19588967

Mild decarboxylative allylation of coumarins.

Ranjan Jana1, Rushi Trivedi, Jon A Tunge.   

Abstract

Allyl esters of 3-carboxylcoumarins undergo facile decarboxylative coupling at just 25-50 degrees C. This represents the first extension of decarboxylative C-C bond-forming reactions to the coupling of aromatics with sp(3)-hybridized electrophiles. Finally, the same concept can be applied to the sp(2)-sp(3) couplings of pyrones and flavones. Thus, a variety of biologically important heteroaromatics can be readily functionalized without the need for strong bases or stoichiometric organometallics that are typically required for more standard cross-coupling reactions.

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Year:  2009        PMID: 19588967      PMCID: PMC2878741          DOI: 10.1021/ol901288r

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


  18 in total

1.  A versatile hexadiene synthesis by decarboxylative sp(3)-sp(3) coupling/cope rearrangement.

Authors:  Shelli R Waetzig; Dinesh K Rayabarapu; Jimmie D Weaver; Jon A Tunge
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-24       Impact factor: 15.336

2.  Regio- and diastereoselective decarboxylative coupling of heteroaromatic alkanes.

Authors:  Shelli R Waetzig; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2007-03-20       Impact factor: 15.419

3.  Unexpected intermolecular pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners.

Authors:  Pat Forgione; Marie-Christine Brochu; Miguel St-Onge; Kris H Thesen; Murray D Bailey; François Bilodeau
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

Review 4.  Coumarins.

Authors:  A Estévez-Braun; A G González
Journal:  Nat Prod Rep       Date:  1997-10       Impact factor: 13.423

5.  Catalytic decarboxylative sp-sp3 coupling.

Authors:  Dinesh Kumar Rayabarapu; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2005-10-05       Impact factor: 15.419

6.  Synthesis of 4-substituted coumarins via the palladium-catalyzed cross-couplings of 4-tosylcoumarins with terminal acetylenes and organozinc reagents.

Authors:  J Wu; Y Liao; Z Yang
Journal:  J Org Chem       Date:  2001-05-18       Impact factor: 4.354

7.  Decarboxylative allylation using sulfones as surrogates of alkanes.

Authors:  Jimmie D Weaver; Jon A Tunge
Journal:  Org Lett       Date:  2008-09-12       Impact factor: 6.005

8.  Palladium/copper-catalyzed decarboxylative cross-coupling of aryl chlorides with potassium carboxylates.

Authors:  Lukas J Goossen; Bettina Zimmermann; Thomas Knauber
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  General and efficient route for the synthesis of 3,4-disubstituted coumarins via Pd-catalyzed site-selective cross-coupling reactions.

Authors:  Liang Zhang; Tianhao Meng; Renhua Fan; Jie Wu
Journal:  J Org Chem       Date:  2007-08-18       Impact factor: 4.354

10.  Chromen-based TNF-alpha converting enzyme (TACE) inhibitors: design, synthesis, and biological evaluation.

Authors:  Kwangwoo Chun; Song-Kyu Park; Hwan Mook Kim; Yongseok Choi; Myung-Hwa Kim; Chun-Ho Park; Bo-Young Joe; Tae Gyu Chun; Hyun-Moo Choi; Hee-Yoon Lee; Sung Hee Hong; Myung Sook Kim; Ky-Youb Nam; Gyoonhee Han
Journal:  Bioorg Med Chem       Date:  2007-09-14       Impact factor: 3.641

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  6 in total

Review 1.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

2.  Migratory decarboxylative coupling of coumarins: synthetic and mechanistic aspects.

Authors:  Ranjan Jana; James J Partridge; Jon A Tunge
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

3.  Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox.

Authors:  Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-09-15       Impact factor: 15.419

4.  Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Authors:  Kalicharan Cattopadhyay; Antonio Recio; Jon A Tunge
Journal:  Org Biomol Chem       Date:  2012-07-25       Impact factor: 3.876

5.  Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles.

Authors:  Kalicharan Chattopadhyay; Erik Fenster; Alexander J Grenning; Jon A Tunge
Journal:  Beilstein J Org Chem       Date:  2012-07-27       Impact factor: 2.883

6.  Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes.

Authors:  Ghina'a I Abu Deiab; Mohammed H Al-Huniti; I F Dempsey Hyatt; Emma E Nagy; Kristen E Gettys; Sommayah S Sayed; Christine M Joliat; Paige E Daniel; Rupa M Vummalaneni; Andrew T Morehead; Andrew L Sargent; Mitchell P Croatt
Journal:  Beilstein J Org Chem       Date:  2017-02-28       Impact factor: 2.883

  6 in total

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