Straightforward Transformation
of Pentafluorobenzaldehyde into 4-Aryloxy-2,3,5,6-tetrafluorobenzaldehydes

Daniel T. Gryko; Dagmara Wyrostek; Agnieszka Nowak-Król; Katarzyna Abramczyk; Maciej K. Rogacki

doi:10.1055/s-0028-1083246

PAPER

Straightforward Transformation of Pentafluorobenzaldehyde into 4-Aryloxy-2,3,5,6-tetrafluorobenzaldehydes

Daniel T. Gryko*, Dagmara Wyrostek, Agnieszka Nowak-Król, Katarzyna Abramczyk, Maciej K. Rogacki
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: daniel@icho.edu.pl;

Abstract

All articles of this category

Abstract

A new and practical process leading to 4-aryloxy-2,3,5,6-tetrafluorobenzaldehydes has been developed. The title skeleton is assembled in a convergent fashion from phenols and pentafluorobenzaldehyde via a nucleophilic substitution in the presence of inorganic fluorides. Scope and limitation studies have been conducted, revealing that the methodology is diversity tolerant, facilitating the introduction of various aryl and heteroaryl substituents. Altogether, 12 aldehydes were prepared in 14-93% yield.

Key words

phenols - ethers - fluorine - nucleophilic aromatic substitution - aldehydes

Full Text

References

1a Isanbor C. O’Hagan D. J. Fluorine Chem. 2006, 127: 303

1b Ismail FMD. J. Fluorine Chem. 2002, 118: 27

1c Kirk KL. J. Fluorine Chem. 2006, 127: 1013

1d Sun S. Adejare A. Curr. Top. Med. Chem. 2006, 6: 1457

2a Sessler JL. Seidel D. Angew. Chem. Int. Ed. 2003, 42: 5134

2b Gryko DT. Koszarna B. Eur. J. Org. Chem. 2005, 3314

2c Gryko DT. Piechowska J. Jaworski JS. Gaūzowski M. Tasior M. Cembor M. Butenschön H. New J. Chem. 2007, 31: 1613

2d Shen J. Shao J. Ou Z. E W. Koszarna B. Gryko DT. Kadish KM. Inorg. Chem. 2006, 45: 2251

2e Gryko DT. Koszarna B. Synthesis 2004, 2205

3 Shaw SJ. Elgie KJ. Edwards C. Boyle RW. Tetrahedron Lett. 1999, 40: 1595

4 Elgie KJ. Scobie M. Boyle RW. Tetrahedron Lett. 2000, 41: 2753

5a Weiss R. Puhlhofer F. Jux N. Merz K. Angew. Chem. Int. Ed. 2002, 41: 3815

5b Samaroo D. Soll CE. Todaro LJ. Drain CM. Org. Lett. 2006, 8: 4985

6a Yeager GW. Schissel DN. Synthesis 1991, 63

6b Magdolen P. Mečiarová M. Toma Š. Tetrahedron 2001, 57: 4781

7 Varala R. Ramu E. Alam MM. Adapa SR. Synlett 2004, 1747

8a Beugelmans R. Bigot A. Zhu J. Tetrahedron Lett. 1994, 35: 5649

8b Beugelmans R. Singh GP. Zhu J. Tetrahedron Lett. 1993, 34: 7741

9 Beugelmans R. Bourdet S. Zhu J. Tetrahedron Lett. 1995, 36: 1279

10a Gryko DT. Clausen C. Roth KM. Dontha N. Bocian DF. Kuhr WG. Lindsey JS. J. Org. Chem. 2000, 65: 7345

10b Gryko DT. Koszarna B. Org. Biomol. Chem. 2003, 1: 350

11 Keana JFW. Cai SX. J. Org. Chem. 1990, 55: 3640

12a Bolton R. Sandall JPB. J. Chem. Soc., Perkin Trans. 2 1978, 1288

12b Miller J. Parker AJ. J. Am. Chem. Soc. 1961, 83: 117

13 Loim NM. Kelbyscheva ES. Izv. Akad. Nauk, Ser. Khim. 2004, 1995

14a Vorozhtsov NN. Yakobson GG. Zh. Obshch. Khim. 1958, 28: 40; Chem. Abstr. 1958, 52, 12784

14b Drayton CJ. Flowers WT. Haszeldine RN. J. Chem. Soc. D 1970, 662

14c Schmittling EA. Sawyer JS. J. Org. Chem. 1993, 58: 3229

14d Beugelmans R. Bigot A. Zhu J. Tetrahedron Lett. 1994, 35: 5649

15 Grabchev I. Moneva I. Bojinov V. Guittonneau S. J. Mat. Chem. 2000, 10: 1291