Organoselenosilane-Mediated
Selective Mild Access to Selenolesters, Selenoanhydrides
and Diacyl Diselenides

Antonella Capperucci; Alessandro Degl’Innocenti; Caterina Tiberi

doi:10.1055/s-0030-1261195

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Synlett 2011(15): 2248-2252
DOI: 10.1055/s-0030-1261195

LETTER

Organoselenosilane-Mediated Selective Mild Access to Selenolesters, Selenoanhydrides and Diacyl Diselenides

Antonella Capperucci*, Alessandro Degl’Innocenti*, Caterina Tiberi
Department of Chemistry ‘Ugo Schiff’, University of Florence, Via della Lastruccia 3-13, 50019 Sesto Fiorentino (Firenze), Italy
Fax: +39(055)4573585; e-Mail: alessandro.deglinnocenti@unifi.it;

Further Information

Publication History

Received 20 June 2011
Publication Date:
24 August 2011 (online)

Abstract
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Abstract

Reaction of acyl chlorides with phenylselenotrimethylsilane promoted by TBAF afforded a mild general access to selenolesters in good yields. When acyl chlorides were reacted with bis(trimethylsilyl)selenide (HMDSS) in 2:1 or 1:1 ratio a selective entry to selenoanhydrides or diacyl diselenides respectively was obtained.

Key words

selenosilanes - selenolesters - diacyl selenides - diacyl diselenides - fluoride ion

References and Notes

For example, see:
1a Procter DJ. J. Chem. Soc., Perkin Trans. 1 2000, 835

Google Scholar
1b Organoselenium Chemistry: A Practical Approach Back TG. Oxford University Press; Oxford: 1999.

Google Scholar
1c Comasseto JV. Ling LW. Petragnani N. Stefani HA. Synthesis 1997, 373

Google Scholar
1d Krief A. Comprehensive Organometallic Chemistry Vol. 11: Abel EW. Stone EGA. Wilkinson G. Pergamon; Oxford: 1995. p.515

Google Scholar
1e Krief A. Hevesi L. Organoselenium Chemistry I Springer; Berlin: 1988.

Google Scholar
See also:
2a Braga AL. Lüdtke DS. Vargas F. Braga RC. Synlett 2006, 1453

Google Scholar
2b Braga AL. Vargas F. Sehnem JA. Braga RC. J. Org. Chem. 2005, 70: 9021

Google Scholar
2c Braga AL. Lüdtke DS. Sehnem JA. Alberto EE. Tetrahedron 2005, 61: 11664

Google Scholar
2d Braga AL. Paixão MW. Lüdtke DS. Silveira CC. Rodrigues OED. Org. Lett. 2003, 5: 3635

Google Scholar
3a Nogueira CW. Zeni G. Rocha JBT. Chem. Rev. 2004, 104: 6255

Google Scholar
3b Mugesh G. duMont W.-W. Sies H. Chem. Rev. 2001, 101: 2125

Google Scholar
3c Nicolaou KC. Petasis NA. Selenium in Natural Products Synthesis CIS; Philadelphia: 1984; and references therein.

Google Scholar
3d Klayman DL. Günter WHH. In Organoselenium Compounds: Their Chemistry and Biology Wiley Interscience; New York: 1973.

Google Scholar
4 Pheninger J. Heuberger C. Graf W. Helv. Chim. Acta 1980, 63: 2328

Crossref Google Scholar
5a Keck G. Grier MC. Synlett 1999, 1657

Google Scholar
5b Boger DL. Mathvink RJ. J. Org. Chem. 1992, 57: 1429

Google Scholar
5c Chen C. Crich D. Papadatos A. J. Am. Chem. Soc. 1992, 114: 8313

Google Scholar
6 Hiiro T. Morita Y. Inoue T. Kambe N. Ogawa A. Ryu I. Sonoda N. J. Am. Chem. Soc. 1990, 112: 455

Crossref Google Scholar
7a Sviridov AF. Ermolenko MS. Yashunsky DV. Kochetkov NK. Tetrahedron Lett. 1983, 24: 4355

Google Scholar
7b Anderson RJ. Henrick CA. Rosenblum LD. J. Am. Chem. Soc. 1974, 96: 3654

Google Scholar
7c Mukaiyama T. Araki M. Takei H. J. Am. Chem. Soc. 1973, 95: 4763

Google Scholar
8a McGarvey GJ. Williams JM. Hiner RN. Matsubara Y. Oh T. J. Am. Chem. Soc. 1986, 108: 4943

Google Scholar
8b Conrow R. Portoghese P. J. Org. Chem. 1986, 51: 938

Google Scholar
8c Back TG. Kerr RG. Tetrahedron 1985, 41: 4759

Google Scholar
9a Suh K.-H. Choo D.-J. Tetrahedron Lett. 1995, 36: 6109

Google Scholar
9b Kobayashi S. Uchiro H. Fujishita Y. Shiina I. Mukaiyama T. J. Am. Chem. Soc. 1991, 113: 4247

Google Scholar
10 Renson M. Draguet C. Bull. Soc. Chim. Belg. 1962, 71: 260

Crossref Google Scholar
11a Ren K. Wang M. Liu P. Wang L. Synthesis 2010, 1078

Google Scholar
11b Movassagh B. Mirshojaei F. Monatsh. Chem. 2003, 134: 831

Google Scholar
11c Chen R. Zhang Y. Synth. Commun. 2000, 30: 1331

Google Scholar
11d Zang Y. Yu Y. Lin R. Synth. Commun. 1993, 23: 189

Google Scholar
12a Zhang SL. Tian FS. Li GA. Wang YL. Chin. Chem. Lett. 2002, 13: 9

Google Scholar
12b Xu XH. Liu WQ. Chin. Chem. Lett. 2002, 13: 283

Google Scholar
12c Wang L. Zhang Y. Synth. Commun. 1999, 29: 3107

Google Scholar
13a Wallner OA. Szabo KJ. J. Org. Chem. 2005, 70: 9215

Google Scholar
13b Nishiyama Y. Kawamatsu H. Funato S. Tokunaga K. Sonoda N. J. Org. Chem. 2003, 68: 3599

Google Scholar
13c Nishiyama Y. Tokunaga K. Kawamatsu H. Sonoda N. Tetrahedron Lett. 2002, 43: 1507

Google Scholar
13d Beletskaya I. Sigeev AS. Peregudov AS. Petrovskii PV. Russ. J. Org. Chem. 2001, 37: 1703

Google Scholar
13e Schiesser CH. Skidmore MA. J. Chem. Soc., Perkin Trans. 1 1997, 2689

Google Scholar
14a Tiecco M. Testaferri L. Temperini A. Bagnoli L. Marini F. Santi C. Terlizzi R. Eur. J. Org. Chem. 2004, 3447

Google Scholar
14b Braga AL. Martins TLC. Silveira CC. Rodrigues OE. Tetrahedron 2001, 47: 3297

Google Scholar
14c Hoshi M. Masuda Y. Arase A. Bull. Chem. Soc. Jpn. 1988, 61: 3764

Google Scholar
15 Grieco PA. Yokoyama Y. Williams E. J. Org. Chem. 1978, 43: 1283

Crossref Google Scholar
16a Marin G. Braga AL. Rosa AL. Galetta FZ. Burrow RA. Gallardo H. Paixão MW. Tetrahedron 2009, 65: 4614

Google Scholar
16b Munbunjong W. Lee EH. Ngernmaneerat P. Kim SJ. Singh G. Chavasiri W. Jang DO. Tetrahedron 2009, 65: 2467

Google Scholar
16c Braga AL. Schneider PH. Paixão MW. Deobald AM. Tetrahedron Lett. 2006, 47: 7195

Google Scholar
16d Ranu BC. Mandal T. J. Org. Chem. 2004, 69: 5793

Google Scholar
17 Tabarelli G. Alberto EE. Deobald AM. Marin G. Rodrigues OED. Dornelles L. Braga AL. Tetrahedron Lett. 2010, 51: 5278

Google Scholar
18a Dan W. Deng H. Chen J. Liu M. Ding J. Wu H. Tetrahedron 2010, 66: 7384

Google Scholar
18b Qian H. Shao L.-X. Huang X. Synlett 2001, 1571

Google Scholar
18c Fujiwara S.-I. Asai A. Shinike T. Kambe N. Sonoda N. J. Org. Chem. 1998, 63: 1724

Google Scholar
18d Inoue T. Takeda T. Kambe N. Ogawa A. Ryu I. Sonoda N. J. Org. Chem. 1994, 59: 5824

Google Scholar
18e Kozikowski AP. Ames A. Tetrahedron 1985, 41: 4821

Google Scholar
18f Grieco PA. Jaw JY. Claremon DA. Nicolau KC. J. Org. Chem. 1981, 46: 1215

Google Scholar
18g Back TG. Collins S. Kerr RG. J. Org. Chem. 1981, 46: 1564

Google Scholar
19a Degl’Innocenti A. Pollicino S. Capperucci A. Chem. Commun. 2006, 4881

Google Scholar
19b Degl’Innocenti A. Capperucci A. Malesci I. Castagnoli G. Acciai M. Nocentini T. Pollicino S. Synlett 2006, 2439

Google Scholar
19c Degl’Innocenti A. Capperucci A. Eur. J. Org. Chem. 2000, 2171

Google Scholar
19d Capperucci A. Degl’Innocenti A. Leriverend A. Metzner P. J. Org. Chem. 1996, 61: 7174

Google Scholar
19e Capperucci A. Ferrara MC. Degl’Innocenti A. Bonini BF. Mazzanti G. Zani P. Ricci A. Tetrahedron Lett. 1994, 35: 16

Google Scholar
19f Capperucci A. Ferrara MC. Degl’Innocenti A. Bonini BF. Mazzanti G. Zani P. Ricci A. Synlett 1992, 880

Google Scholar
19g Ricci A. Degl’Innocenti A. Mordini A. Reginato G. Colotta V. Gazz. Chim. It. 1987, 117: 645

Google Scholar
19h Ricci A. Degl’Innocenti A. Chimichi S. Fiorenza M. Rossini G. Bestman HJ. J. Org. Chem. 1985, 50: 130

Google Scholar
20a Capperucci A. Tiberi C. Pollicino S. Degl’Innocenti A. Tetrahedron Lett. 2009, 50: 2808

Google Scholar
20b Capperucci A. Degl’Innocenti A. Pollicino S. Acciai M. Castagnoli G. Malesci I. Heteroat. Chem. 2007, 18: 516

Google Scholar
20c Degl’Innocenti A. Capperucci A. Nocentini T. Tetrahedron Lett. 2000, 42: 4557

Google Scholar
21a Degl’Innocenti A. Capperucci A. Castagnoli G. Malesci I. Synlett 2005, 1965

Google Scholar
21b Bouillon J.-P. Capperucci A. Portella C. Degl’Innocenti A. Tetrahedron Lett. 2004, 45: 87

Google Scholar
21c Capperucci A. Degl’Innocenti A. Nocentini T. Biondi S. Dini F.
J. Organomet. Chem. 2003, 686: 363

Google Scholar
21d Capperucci A. Degl’Innocenti A. Biondi S. Nocentini T. Rinaudo G. Tetrahedron Lett. 2003, 44: 2831

Google Scholar
21e Degl’Innocenti A. Capperucci A. Oniciu D. Katritzky AR. J. Org. Chem. 2000, 65: 9206

Google Scholar
21f Degl’Innocenti A. Capperucci A. Scafato P. Mecca T. Reginato G. Mordini A. Synlett 1999, 1739

Google Scholar
21g Ricci A. Degl’Innocenti A. Capperucci A. Reginato G. J. Org. Chem. 1989, 54: 19

Google Scholar
22 Degl’Innocenti A. Capperucci A. Cerreti A. Pollicino S. Scapecchi S. Malesci I. Castagnoli G. Synlett 2005, 3063

Article in Thieme Connect Google Scholar
23 Degl’Innocenti A. Capperucci A. Acciai M. Tiberi C. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184: 1621

Crossref Google Scholar
24 Degl’Innocenti A. Capperucci A. Castagnoli G. Malesci I. Tiberi C. Innocenti B. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183: 966

Crossref Google Scholar
26a Lange H. Herzog U. J. Organomet. Chem. 2002, 660: 36

Google Scholar
26b Detty MR. Seidler MD. J. Org. Chem. 1982, 47: 1354

Google Scholar
27a Niyomura O. Tani K. Kato S. Heteroat. Chem. 1999, 10: 373

Google Scholar
27b Kageyama H. Kido K. Kato S. Murai T.
J. Chem. Soc., Perkin Trans. 1 1994, 1083

Google Scholar
27c Kato S. Kageyama H. Kawahara Y. Murai T. Ishihara H. Chem. Ber. 1992, 125: 417

Google Scholar
27d Wang J.-X. Wang C.-H. Wang W.-F. Cui W.-F. Hu Y.-L. Zang S.-S. J. Chem. Res., Synop. 1990, 230

Google Scholar
27e Nishiyama Y. Katsuura A. Okamoto Y. Hamanaka S. Chem. Lett. 1989, 18: 1825

Google Scholar
27f Ishihara H. Kato S. Tetrahedron Lett. 1972, 3751

Google Scholar
27g Jensen KA. Bøje L. Henriksen L. Acta Chem. Scand. 1972, 26: 1465

Google Scholar
28a Zhao H.-R. Zhao X.-J. Huang X. Synth. Commun. 2002, 32: 3383

Google Scholar
28b Zhao H.-R. Zhao X.-J. Huang X. Chin. Chem. Lett. 2001, 12: 873

Google Scholar
29a Koketsu M. Nada F. Hiramatsu S. Ishihara H.
J. Chem. Soc., Perkin Trans. 1 2002, 737

Google Scholar
29b Ishihara H. Koketsu M. Fukuta Y. Nada F. J. Am. Chem. Soc. 2001, 123: 8408

Google Scholar
32 Kageyama H. Murai T. Kanda T. Kato S. J. Am. Chem. Soc. 1994, 116: 2195

Crossref Google Scholar
See also:
33a Sawant AD. Raut DG. Darvatkar NB. Salunkhe MM. Green Chem. Lett. Rev. 2011, 4: 41

Google Scholar
33b
Greaves TL. Drummond CJ. Chem. Rev. 2008, 108: 206

Google Scholar
33c Chowdhury S. Mohan RS. Scott JL. Tetrahedron 2007, 63: 2363

Google Scholar
33d Sheldon R. Chem. Commun. 2001, 2399

Google Scholar
33e Wasserscheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772

Google Scholar
33f Welton T. Chem. Rev. 1999, 99: 207

Google Scholar

25

Preparation of Se-Phenyl 2-chloropropaneselenoate (3f): To a solution of 2-chloropropanoyl chloride (30 mg, 0.24 mmol) in anhyd THF (0.5 mL) was added under an inert atmosphere phenylselenotrimethylsilane (71 µL, 0.28 mmol). TBAF (50 µL, 1 M THF solution, 0.05 mmol) was added dropwise at 0 ˚C. The reaction was warmed to r.t. and stirred overnight. The mixture was then extracted with Et₂O, washed with brine and dried over Na₂SO₄. Filtration and evaporation of the solvent gave the crude 3f as a yellow oil, which was purified by TLC on silica gel (n-hexane-CH₂Cl₂, 2:1). Yield: 63%. ^¹H NMR (200 MHz, CDCl₃): δ = 1.75 (d, 3 H, J = 7.0 Hz), 4.58 (q, 1 H, J = 7.0 Hz), 7.43-7.46 (m, 3 H), 7.51-7.55 (m, 2 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 22.1, 63.7, 127.5, 129.3, 130.6, 131.3, 200.4. ⁷⁷Se (38 MHz, CDCl₃): δ = 650.6. MS: m/z (%) = 248 (26) [M⁺], 192 (22), 158 (39), 91 (44), 78 (55), 63 (100).

30

Synthesis of 4-Methoxybenzoic Selenoanhydride (5c): A solution of 4-methoxybenzoyl chloride (24 µL, 0.18 mmol) and TBAF (1 M in THF, 18 µL, 0.018 mmol) in anhyd THF (0.5 mL) was cooled under atmosphere at 0 ˚C, and treated dropwise with bis(trimethylsilyl)selenide (HMDSS; 21 mg, 0.09 mmol). The red mixture turned to pale yellow after few minutes. After warming to r.t., and stirring for 2 h, the solution was diluted with Et₂O, washed with brine and dried over Na₂SO₄. The crude product was purified by flash column chromatography (n-hexane-CH₂Cl₂, 1:1) to afford 5c as a yellow solid (24 mg, 75%). ^¹H NMR (200 MHz, CDCl₃): δ = 3.88 (s, 6 H), 6.93-6.98 (m, 4 H), 7.92-7.96 (m, 4 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 55.6, 114.1, 130.9, 131.5, 164.5, 185.9. ⁷⁷Se (38 MHz, CDCl₃): δ = 730.0.

31

Preparation of 4-Methoxybenzoic Diselenoperoxy-anhydride (6c): A solution of 4-methoxybenzoyl chloride (24 µL, 0.18 mmol) in anhyd THF (0.5 mL) was added under an inert atmosphere with HMDSS (44 mg, 0.19 mmol) and it was cooled to 0 ˚C. TBAF (1 M in THF, 38 µL, 0.038 mmol) was then added dropwise. The red mixture so formed was warmed to r.t. and stirred for 2 h. Upon quenching with brine, the red solution turned slowly to pale yellow. Extraction with Et₂O, drying over Na₂SO₄ and removal of the solvent under vacuum afforded the crude product, which was purified by flash column chromatography (n-hexane-CH₂Cl₂, 1:1) to produce 6c as a yellow solid (55 mg, 71%). ^¹H NMR (200 MHz, CDCl₃):
δ = 3.88 (s, 6 H), 6.92-6.98 (m, 4 H), 7.91-8.07 (m, 4 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 55.6, 114.2, 129.3, 130.5, 164.4, 186.9. ⁷⁷Se (38 MHz, CDCl₃): δ = 598.5.