Acylation of Ferrocene and a 1,1′‐Diphosphaferrocene with Acyl Trifluoroacetates in the Presence of Trifluoromethanesulfonic (Triflic) Acid or Some Metal Triflates

References

• Togni , A. and Hayashi , T. 1995 . Ferrocenes Edited by: Togni , A. and Hayashi , T. New York : VCH .
   Google Scholar
• Long , N. J. 1995 . Metallocenes London : Blackwell .
   Google Scholar
• Richards , C. J. and Locke , A. J. 1998 . Recent advances in the generation of non‐racemic ferrocene derivatives and their application to asymmetric synthesis . Tetrahedron: Asymmetr. , 9 : 2377
   Web of Science ®Google Scholar
• Togni , A. 1996 . Planar chiral ferrocenes: synthetic methods and applications . Angew Chem. Int. Edit. Engl. , 35 : 1475 [CROSSREF]
   Google Scholar
• Togni , A. , Dorta , R. , Koelner , C. and Pioda , G. 1998 . Some new aspects of asymmetric catalysis with chiral ferrocenyl ligands . Pure. Appl. Chem. , 70 : 1477
   Google Scholar
• Hudson , R. D.A. 2001 . Ferrocene polymers: current architectures, synthesis and utility . J. Organomet. Chem. , 637–639 : 47 [CROSSREF]
   Web of Science ®Google Scholar
• Plenio , H. , Hermann , J. and Sehring , A. 2000 . Optically and redox‐active ferrocenylacetylene polymers and oligomers . Chem. Eur. J. , 6 : 1820 [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Newkome , G. R. , He , E. and Moorefield , C. N. 1999 . Suprasupermolecules with novel properties: metallodendrimers . Chem. Rev. , 99 : 1689 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Alvarez , J. , Ren , T. and Kaifer , A. E. 2001 . Redox potential selection in a new class of dendrimers containing multiple ferrocene centers . Organometallics , 20 : 3543 [CROSSREF]
   Google Scholar
• Di Bella , S. 2001 . Second‐order nonlinear optical properties of transition metal complexes . Chem. Soc. Rev. , 30 : 355 [CROSSREF]
   Web of Science ®Google Scholar
• Whittall , I. R. , McDonagh , A. M. , Humphrey , M. G. and Samoc , M. 1998 . “ Organometallic complexes in nonlinear optics I: second‐order nonlinearities ” . In Adv. Organomet. Chem Edited by: Stone , F. G.A. and West , R. Vol. 42 , 291 New York : Academic .
   Google Scholar
• Long , N. J. 1995 . Organometallic compounds for nonlinear optics‐ the search for enlightenment . Angew. Chem. Int. Ed. Engl. , 34 : 21 [CROSSREF]
   Web of Science ®Google Scholar
• Engratkul , C. and Sita , L. R. 2001 . Ferrocene‐based nanoelectronics: 2.5‐diethynylpyridine as a reversible switching element . Nanoletters , 1 : 541
   Google Scholar
• Gryko , D. T. , Zhao , F. , Yasseri , A. A. , Roth , K. M. , Bocian , D. F. , Kuhr , W. G. and Lindsey , J. D. 2000 . Synthesis of thiol‐derivatized ferrocene‐porphyrins for studies of multibit information storage . J. Org. Chem. , 65 : 7356 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Beer , P. D. 1998 . Transition‐metal receptor systems for the selective recognition and sensing of anionic quest species . Acc. Chem. Res. , 31 : 71 [CROSSREF]
   Web of Science ®Google Scholar
• Beer , P. D. 1996 . Anion selective recognition and optical/electrochemical sensing by novel transition‐metal receptor systems . Chem. Commun. , : 689 [CROSSREF]
   Google Scholar
• Beer , P. D. 1989 . Redox responsive macrocyclic receptor molecules containing transition metal redox centres . Chem. Soc. Rev. , 18 : 409 [CROSSREF]
   Web of Science ®Google Scholar
• Tsukube , H. , Fukui , H. and Shinoda , S. 2001 . Synergic binding and chirality sensing of unprotected amino acids with ferrocene‐carboxylic acid‐crown ether conjugate . Tetrahedron Lett. , 42 : 7583 [CROSSREF]
   Google Scholar
• Fery‐Forgues , S. and Delaraux‐Nicot , B. 2000 . Ferrocene and ferrocenyl derivatives in luminescent systems . J. Photochem. Photobiol. A: Chem. , 132 : 137 [CROSSREF]
   Web of Science ®Google Scholar
• Yamaguchi , Y. and Kutal , C. 2000 . Benzoyl‐substituted ferrocenes: an attractive new class of anionic photoinitiators . Macromolecules , 33 : 1152 [CROSSREF]
   Google Scholar
• Uosaki , K. , Kondo , T. , Zhang , X. Q. and Yanagida , M. 1997 . Very efficient visible‐light induced uphill electron transfer at a self‐assembled monolayer with a porphyrin‐ferrocene‐thiol linked molecule . J. Am. Chem. Soc. , 119 : 8367 [CROSSREF]
   Web of Science ®Google Scholar
• Top , S. , Vessières , A. , Cabestaing , C. , Laios , I. , Leclerq , G. , Provot , C. and Jaouen , G. 2001 . Studies on organometallic selective estrogen receptor modulators (SERMs). Dual activity in the hydroxy‐ferrocifen series . J. Organomet. Chem. , 637–639 : 500 [CROSSREF]
   Web of Science ®Google Scholar
• Rosenblum , M. 1965 . Chemistry of the Iron Group Metallocenes New York : Wiley and Sons .
   Google Scholar
• Jary , W. G. , Mahler , A. K. , Purkathofer , T. and Baumgartner , J. 2001 . A convenient synthesis of E‐alkenylferrocenes . J. Organomet. Chem. , 629 : 209 [CROSSREF]
   Google Scholar
• Misterkiewicz , B. 1982 . A simple synthesis and purification of 1‐ferrocenylalkyl alcohols . J. Organomet. Chem. , 224 : 43 [CROSSREF]
   Web of Science ®Google Scholar
• Misterkiewicz , B. , Dabard , R. and Patin , H. 1985 . Substitution electrophile du ferrocene et du dimethylferrocene par les derives carbonyles substitues . Tetrahedron , 41 : 16 [CROSSREF]
   Google Scholar
• Plażuk , D. , Klys , A. , Zakrzewski , J. , Rybarczyk‐Pirek , A. and Olszak , T. A. 2001 . Direct acetoacetylation of ferrocene and a 1,1′‐diphosphaferrocene . Organometallics , 20 : 4448 [CROSSREF]
   Google Scholar
• Plażuk , D. and Zakrzewski , J. 2002 . Friedel–Crafts‐type reaction of ferrocene with β‐ketoesters . J. Org. Chem. , 67 : 8672 [CROSSREF]
   PubMedGoogle Scholar
• Kobayashi , S. , Sugiura , M. , Kitagawa , H. and Lam , W.‐L. 2002 . Rare‐earth metal triflates in organic synthesis . Chem. Rev. , 102 : 2227 (and references cited therein) [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Hwang , J. P. , Surya Prakash , G. K. and Olah , G. A. 2000 . Trifluoromethanesulfonic acid catalyzed novel Friedel–Crafts acylation of aromatics with methyl benzoate . Tetrahedron , 56 : 7199 [CROSSREF]
   Google Scholar
• Klumpp , D. A. , Yeung , Y. K. , Surya Prakash , G. K. and Olah , G. A. 1998 . Superacid activated condensation of parabanic acid and derivatives with arenes. A new synthesis of phenytoin and 5,5‐diarylhydantoins . SynLett. , : 918
   Google Scholar
• Klumpp , D. A. , Sanchez , G. V. , Aguirre , S. L. Jr. , Zhang , Y. and de Leon , S. 2002 . Chemistry of dicationic electrophiles: superacid‐catalyzed reactions of aminoacetals . J. Org. Chem. , 67 : 5028 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Effenberger , F. and Epple , G. 1972 . Trifluoromethanesulfonic‐carboxylic anhydrides, highly reactive acylating agents . Angew. Chem. Int. Edit. Engl. , 11 : 299 [CROSSREF]
   Google Scholar
• Effenberger , F. , Eberhard , J. K. and Maier , A. 1996 . The first unequivocal evidence of the reacting nucleophile in aromatic acylation reactions . J. Am. Chem. Soc. , 118 : 12572 [CROSSREF]
   Google Scholar
• Smyth , T. B. and Corby , B. W. 1997 . Industrially viable alternative to the Friedel–Crafts acylation reaction: tamoxifen case study . Org. Process Res. Dev. , 1 : 264 [CROSSREF]
   Web of Science ®Google Scholar
• Smyth , T. B. and Corby , B. W. 1998 . Toward a clean alternative to Friedel–Crafts acylation: in situ formation, observation and reaction of an acyl bis(trifluoroacetyl)phosphate and related structures . J. Org. Chem. , 63 : 8946 [CROSSREF]
   Web of Science ®Google Scholar
• Darin , V. A. , Neto , A. F. , Miller , J. , de Freitas Alfonso , M. M. , Fonsatti , H. C. and Borges , A. D.L. 1998 . Boron trifloride etherate as catalysts in acylation of ferrocene . J. Prakt. Chem. , 341 : 588 [CROSSREF]
   Google Scholar
• Vukićević , M. D. , Ratkowić , Z. D. , Teodorović , A. V. , Stojanović , G. S. and Vukicević , R. D. 2002 . Acylation of ferrocene: a new approach . Tetrahedron , 58 : 9001 [CROSSREF]
   Web of Science ®Google Scholar
• Roberts , R. M.G. and Wells , A. S. 1986 . Trifluoromethanesulphonic acid as a catalyst in acylation of phosphaferrocenes . Inorg. Chim. Acta , 112 : 167 [CROSSREF]
   Google Scholar
• Galli , C. 1979 . Acylation of arenes and heteroarenes with in situ generated acyl trifluoroacetatates . Synthesis , : 303 [CROSSREF]
   Google Scholar
• Ranu , B. C. , Jana , U. and Majee , A. 1999 . Selective monoacylation of ferrocene: an eco-friendly procedure on the solid phase of alumina . Green Chem. , : 33 [CROSSREF]
   Google Scholar
• Dillon , K. B. , Mathey , F. and Nixon , J. F. 1998 . “ π‐Coordination complexes ” . In Phosphorus: The Carbon Copy Chichester : Wiley . Chap. 9
   Google Scholar
• Ashe , A. J. III and Al‐Ahmad , S. 1996 . “ Diheteroferrocenes and related derivatives of the group 15 elements: arsenic, antimony and bismuth ” . In Adv. Organomet. Chem. Edited by: Stone , F. G.A. and West , R. 325 San Diego : Academic Press .
   Google Scholar
• Mathey , F. 2002 . Phosphametallocenes: from discovery to applications . J. Organomet. Chem. , 646 : 15 [CROSSREF]
   Google Scholar
• de Lauzon , G. , Deschamps , B. , Fischer , J. , Mathey , F. and Mitschler , A. 1980 . 1,1′‐Diphosphaferrocenes. Synthesis, basic chemistry and structure . J. Am. Chem. Soc. , 102 : 994
   Web of Science ®Google Scholar
• Mathey , F. and de Lauzon , G. 1986 . “ 3,3′,4,4′‐Tetramethyl‐1,1′‐diphosphaferrocene ” . In Organometallic Synthesis 251 Amsterdam : Elsevier .
   Google Scholar
• Ranson , R. J. and Roberts , R. M.G. 1984 . 13C chemical shifts and carbonyl stretching frequencies as structural probes for ferrocenyl ketones . J. Organomet. Chem. , 80 : 307 [CROSSREF]
   Google Scholar