Literature DB >> 16209485

Synthesis of diethynyltriptycene-linked dipyridyl ligands.

Jeremy J Kodanko1, Anna J Morys, Stephen J Lippard.   

Abstract

[reaction: see text] An efficient route to a new family of dinucleating ligands has been developed. A convergent strategy to these ligands involved dual Sonogashira cross-coupling of 2,3-diethynyltriptycene with a variety of functionally diverse 5-bromopyridines. The resultant ligands were accessed in four steps and 40-50% overall yield from 1,2,4,5-tetrabromobenzene. Synthesis of an imidazole and a quinoline derivative by this method is also described.

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Year:  2005        PMID： 16209485      PMCID： PMC1552108          DOI： 10.1021/ol051700h

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


  9 in total

1.  Protein Radicals in Enzyme Catalysis.

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2.  A concise synthesis of fusaric acid and (S)-(+)-fusarinolic acid.

Authors:  J J Song; N K Yee
Journal:  J Org Chem       Date:  2001-01-26       Impact factor: 4.354

3.  Efficient synthesis of alpha-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates.

Authors:  Morten Jørgensen; Sunwoo Lee; Xiaoxiang Liu; Joanna P Wolkowski; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

4.  Hydroxylation of methane by non-heme diiron enzymes: molecular orbital analysis of C-H bond activation by reactive intermediate Q.

Authors:  Mu-Hyun Baik; Benjamin F Gherman; Richard A Friesner; Stephen J Lippard
Journal:  J Am Chem Soc       Date:  2002-12-11       Impact factor: 15.419

5.  Synthesis of chiral pilocarpine analogues via a C-8 ketone intermediate.

Authors:  Kenneth G Holden; Matthew N Mattson; Kyung Hoi Cha; Henry Rapoport
Journal:  J Org Chem       Date:  2002-08-23       Impact factor: 4.354

Review 6.  Synthetic models for non-heme carboxylate-bridged diiron metalloproteins: strategies and tactics.

Authors:  Edit Y Tshuva; Stephen J Lippard
Journal:  Chem Rev       Date:  2004-02       Impact factor: 60.622

7.  Dioxygen Activation and Methane Hydroxylation by Soluble Methane Monooxygenase: A Tale of Two Irons and Three Proteins A list of abbreviations can be found in Section 7.

Authors:  Maarten Merkx; Daniel A. Kopp; Matthew H. Sazinsky; Jessica L. Blazyk; Jens Müller; Stephen J. Lippard
Journal:  Angew Chem Int Ed Engl       Date:  2001-08-03       Impact factor: 15.336

8.  Modeling the syn disposition of nitrogen donors at the active sites of carboxylate-bridged diiron enzymes. Enforcing dinuclearity and kinetic stability with a 1,2-diethynylbenzene-based ligand.

Authors:  Jane Kuzelka; Joshua R Farrell; Stephen J Lippard
Journal:  Inorg Chem       Date:  2003-12-29       Impact factor: 5.165

9.  Reactions of the diiron enzyme stearoyl-acyl carrier protein desaturase.

Authors:  Brian G Fox; Karen S Lyle; Corina E Rogge
Journal:  Acc Chem Res       Date:  2004-07       Impact factor: 22.384
  9 in total
  8 in total

1.  Modeling the syn disposition of nitrogen donors in non-heme diiron enzymes. Synthesis, characterization, and hydrogen peroxide reactivity of diiron(III) complexes with the syn N-donor ligand H2BPG2DEV.

Authors:  Simone Friedle; Jeremy J Kodanko; Anna J Morys; Takahiro Hayashi; Pierre Moënne-Loccoz; Stephen J Lippard
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

2.  2-Phenoxypyridyl dinucleating ligands for assembly of diiron(II) complexes: efficient reactivity with O(2) to form (mu-Oxo)diiron(III) units.

Authors:  Loi H Do; Stephen J Lippard
Journal:  Inorg Chem       Date:  2009-11-16       Impact factor: 5.165

3.  Toward functional carboxylate-bridged diiron protein mimics: achieving structural stability and conformational flexibility using a macrocylic ligand framework.

Authors:  Loi H Do; Stephen J Lippard
Journal:  J Am Chem Soc       Date:  2011-06-17       Impact factor: 15.419

Review 4.  Current challenges of modeling diiron enzyme active sites for dioxygen activation by biomimetic synthetic complexes.

Authors:  Simone Friedle; Erwin Reisner; Stephen J Lippard
Journal:  Chem Soc Rev       Date:  2010-05-20       Impact factor: 54.564

Review 5.  Evolution of strategies to prepare synthetic mimics of carboxylate-bridged diiron protein active sites.

Authors:  Loi H Do; Stephen J Lippard
Journal:  J Inorg Biochem       Date:  2011-09-14       Impact factor: 4.155

6.  Iron substitution for sodium in a carboxylate-bridged, heterodinuclear sodium-iron complex.

Authors:  Jeremy J Kodanko; Dong Xu; Datong Song; Stephen J Lippard
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

7.  Synthesis and Characterization of a Ditriflate-Bridged, Diiron(II) Complex with Syn-N-Donor Ligands: [Fe(2)(μ-OTf)(2)(PIC(2)DET)(2)](BARF)(2).

Authors:  Jeremy J Kodanko; Stephen J Lippard
Journal:  Inorganica Chim Acta       Date:  2008-03-03       Impact factor: 2.545

8.  Triptycene-based Bis(benzimidazole) Carboxylate-Bridged Biomimetic Diiron(II) Complexes.

Authors:  Yang Li; Chan Myae Myae Soe; Justin J Wilson; Suan Lian Tuang; Ulf-Peter Apfel; Stephen J Lippard
Journal:  Eur J Inorg Chem       Date:  2013-04-01       Impact factor: 2.524
  8 in total

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