Literature DB >> 22113305

Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions.

Amanda F Ward1, Yan Xu, John P Wolfe.   

Abstract

A new method for the construction of 2-substituted and 2,2-disubstituted chromans via Pd-catalyzed carboetherification reactions between aryl/alkenyl halides and 2-(but-3-en-1-yl)phenols is described. These reactions effect formation of a C-O bond and a C-C bond to afford the chroman products in good yield, and also provide stereoselective access to tricyclic chroman derivatives. This journal is © The Royal Society of Chemistry 2012

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Year:  2011        PMID： 22113305      PMCID： PMC3319722          DOI： 10.1039/c1cc15880e

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


  22 in total

1.  Organocatalytic asymmetric sulfa-michael/michael addition reactions: a strategy for the synthesis of highly substituted chromans with a quaternary stereocenter.

Authors:  Xu-Fan Wang; Qiu-Lin Hua; Ying Cheng; Xiao-Lei An; Qing-Qing Yang; Jia-Rong Chen; Wen-Jing Xiao
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

2.  Pd-catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine.

Authors:  Stefano Nicolai; Stéphane Erard; Davinia Fernández González; Jérôme Waser
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

3.  Domino access to highly substituted chromans and isochromans from carbohydrates.

Authors:  Markus Leibeling; Dennis C Koester; Martin Pawliczek; Svenia C Schild; Daniel B Werz
Journal:  Nat Chem Biol       Date:  2010-01-24       Impact factor: 15.040

4.  Polyalthidin: new prenylated benzopyran inhibitor of the mammalian mitochondrial respiratory chain.

Authors:  M C Zafra-Polo; M C González; J R Tormo; E Estornell; D Cortes
Journal:  J Nat Prod       Date:  1996-10       Impact factor: 4.050

5.  Functionalized tetrahydrofurans from alkenols and olefins/alkynes via aerobic oxidation-radical addition cascades.

Authors:  Patrick Fries; Daniel Halter; Alexander Kleinschek; Jens Hartung
Journal:  J Am Chem Soc       Date:  2011-02-24       Impact factor: 15.419

6.  Enantioselective palladium-catalyzed total synthesis of vitamin e by employing a domino Wacker-Heck reaction.

Authors:  Lutz F Tietze; Florian Stecker; Julia Zinngrebe; Konrad M Sommer
Journal:  Chemistry       Date:  2006-11-24       Impact factor: 5.236

7.  Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

Authors:  Guozhu Zhang; Li Cui; Yanzhao Wang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

8.  Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions.

Authors:  Michael B Hay; John P Wolfe
Journal:  Tetrahedron Lett       Date:  2006-04-17       Impact factor: 2.415

Review 9.  Non-antioxidant activities of vitamin E.

Authors:  Jean-Marc Zingg; Angelo Azzi
Journal:  Curr Med Chem       Date:  2004-05       Impact factor: 4.530

10.  Stereoselective synthesis of 4-dehydroxydiversonol employing enantioselective palladium-catalysed domino reactions.

Authors:  Lutz F Tietze; Dirk A Spiegl; Florian Stecker; Julia Major; Christian Raith; Christian Große
Journal:  Chemistry       Date:  2008       Impact factor: 5.020
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  7 in total

1.  Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Authors:  Zachary J Garlets; Derick R White; John P Wolfe
Journal:  Asian J Org Chem       Date:  2017-03-10       Impact factor: 3.319

2.  Enantioselective copper-catalyzed carboetherification of unactivated alkenes.

Authors:  Michael T Bovino; Timothy W Liwosz; Nicole E Kendel; Yan Miller; Nina Tyminska; Eva Zurek; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

3.  Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols.

Authors:  Scott E Denmark; David J P Kornfilt
Journal:  J Org Chem       Date:  2017-03-03       Impact factor: 4.354

4.  Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.

Authors:  Johnathon T Hutt; John P Wolfe
Journal:  Org Chem Front       Date:  2016-08-22       Impact factor: 5.281

5.  Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis.

Authors:  Zhipeng Guan; Xingxing Zhong; Yayu Ye; Xiangwei Li; Hengjiang Cong; Hong Yi; Heng Zhang; Zhiliang Huang; Aiwen Lei
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

6.  Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins.

Authors:  Hongmei Qin; Qimei Xie; Long He
Journal:  RSC Adv       Date:  2022-06-06       Impact factor: 4.036

7.  Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.

Authors:  Stephen E Ammann; Grant T Rice; M Christina White
Journal:  J Am Chem Soc       Date:  2014-07-16       Impact factor: 15.419
  7 in total

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