Literature DB >> 30739958

Lithium bis-catechol borate as an effective reductive quencher in photoredox catalysis.

Martin J Sevrin1, Laura Furst1, John D Nguyen1, James L Collins1, Corey R J Stephenson1.   

Abstract

The use of lithium bis-catechol borate (LiB(cat)2) as a reductive quencher for the photoredox mediated intermolecular C-H functionalization of various heteroaromatics with bromopyrroloindolines is described. LiB(cat)2 offers a financial benefit over state-of-the-art quenchers currently in use while eliminating the side reactions that typically plague these couplings. The advantage of this methodology is highlighted by the synthesis of C3-C2' (-) gliocladin C. Furthermore, additional examples of reactivity with various bromopyrroloindolines sets the stage for expedient routes towards other pharmaceutically active hexahydropyrroloindoline alkaloids and their analogues.

Entities:  

Year:  2018        PMID: 30739958      PMCID: PMC6364986          DOI: 10.1016/j.tet.2018.04.053

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  14 in total

1.  Total synthesis and absolute configuration of nocardioazine B.

Authors:  Mingzhong Wang; Xiangyang Feng; Liangzhen Cai; Zhengshuang Xu; Tao Ye
Journal:  Chem Commun (Camb)       Date:  2012-03-23       Impact factor: 6.222

2.  1H,1'H-[3,3']biindolyl from the terrestrial fungus Gliocladium catenulatum.

Authors:  Brenda V Bertinetti; M Alejandra Rodriguez; Alicia M Godeas; Gabriela M Cabrera
Journal:  J Antibiot (Tokyo)       Date:  2010-09-08       Impact factor: 2.649

3.  Visible light photoredox catalysis: applications in organic synthesis.

Authors:  Jagan M R Narayanam; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2010-06-08       Impact factor: 54.564

4.  Visible light photocatalysis as a greener approach to photochemical synthesis.

Authors:  Tehshik P Yoon; Michael A Ischay; Juana Du
Journal:  Nat Chem       Date:  2010-06-23       Impact factor: 24.427

5.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

6.  Electron transfer photoredox catalysis: intramolecular radical addition to indoles and pyrroles.

Authors:  Joseph W Tucker; Jagan M R Narayanam; Scott W Krabbe; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

7.  Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole.

Authors:  Pau Ruiz-Sanchis; Svetlana A Savina; Fernando Albericio; Mercedes Álvarez
Journal:  Chemistry       Date:  2011-01-12       Impact factor: 5.236

8.  Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts.

Authors:  John D Nguyen; Joseph W Tucker; Marlena D Konieczynska; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2011-03-07       Impact factor: 15.419

9.  Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates.

Authors:  Laura Furst; Bryan S Matsuura; Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

10.  Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: synthesis of (-)-flustramine B.

Authors:  Joel F Austin; Sung-Gon Kim; Christopher J Sinz; Wen-Jing Xiao; David W C MacMillan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

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  1 in total

Review 1.  Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C-H Functionalization.

Authors:  Zhenbo Yuan; Xuanzhong Liu; Changmei Liu; Yan Zhang; Yijian Rao
Journal:  Molecules       Date:  2020-11-12       Impact factor: 4.411

  1 in total

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