Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study

Murat B. Supurgibekov; G. K. Surya Prakash; Valerij A. Nikolaev

doi:10.1055/s-0032-1318309

Synthesis, Table of Contents

Synthesis 2013; 45(9): 1215-1226
DOI: 10.1055/s-0032-1318309

paper

Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study

Murat B. Supurgibekov

^aSaint Petersburg State University, Department of Organic Chemistry, University pr. 26, 198504, Saint Petersburg, Russian Federation Fax: +7(812)4286733 Email: vnikola@VN6646.spb.edu

,

G. K. Surya Prakash*

^bUniversity of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-1661, USA Fax: +1(213)7408607 Email: gprakash@usc.edu

,

Valerij A. Nikolaev*

^aSaint Petersburg State University, Department of Organic Chemistry, University pr. 26, 198504, Saint Petersburg, Russian Federation Fax: +7(812)4286733 Email: vnikola@VN6646.spb.edu

› Author Affiliations

Abstract

All articles of this category

Abstract

Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF₃, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16–37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37–69%). The configuration of the resulting F- and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.

Key words

(perfluoroalkyl)-containing vinyldiazocarbonyl compounds - diazo transfer - Wittig reaction - 1,3-diketones

Full Text

References

References

For reviews on vinylcarbenoids, see:

1a Davies HM. L. Aldrichimica Acta 1997; 30: 107
1b Davies HM. L. Curr. Org. Chem. 1998; 2: 463

2a Zhang Y, Kubicki J, Platz MS. J. Am. Chem. Soc. 2009; 131: 13602
2b Freeman PK. J. Org. Chem. 2009; 74: 830
2c Moss RA, Tian J, Sauers RR, Sheridan RS, Bhakta A, Zuev RS. Org. Lett. 2005; 7: 4645

3a Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. Wiley; New York: 1998: 652
3b Hamaguchi M, Matsubara H, Nagai T. J. Org. Chem. 2001; 66: 5395
3c Hamaguchi M, Takahashi K, Oshima T, Tamura H. Tetrahedron Lett. 2003; 44: 4339

4a Closs GL, Closs LE. J. Am. Chem. Soc. 1961; 83: 2015
4b Pincock JA, Mathur NC. J. Org. Chem. 1982; 47: 3699
4c Price DJ, Jonson RP. J. Am. Chem. Soc. 1985; 107: 2187

5a Davies HM. L, Clark DM, Alligood DB, Eiband GR. Tetrahedron 1987; 43: 4265
5b Davies HM. L, Ahmed G, Churchill MR. J. Am. Chem. Soc. 1996; 118: 10774
5c Davies HM. L, Calvo R, Ahmed G. Tetrahedron Lett. 1997; 38: 1737
5d Davies HM. L. Adv. Cycloaddit. 1999; 5: 119
5e Reddy RP, Davies HM. L. J. Am. Chem. Soc. 2007; 129: 10312

6a Nikolaev VA, Zakharova VM, Hennig L. J. Fluorine Chem. 2007; 128: 507
6b Supurgibekov MB, Hennig L, Schulze B, Nikolaev VA. Russ. J. Org. Chem. 2008; 44: 1840
6c Supurgibekov MB, Zakharova VM, Sieler J, Nikolaev VA. Tetrahedron Lett. 2011; 52: 341

7 From hereon, we use the ‘cis’ and ‘trans’ designation of spatial arrangement of functional groups (CO₂Alk, CN₂) around the vinyl double bond, ignoring the priority of the CF₃ substituent, since application of the IUPAC Z,E nomenclature in this case implies the same Z or E symbols for (fluoroalkyl)-containing and fluorine-free vinyl substrates with opposite configuration.

8a Regitz M. Angew. Chem., Int. Ed. Engl. 1967; 6: 733
8b Regitz M, Maas G. Diazo Compounds. Properties and Synthesis . Academic Press; New York: 1986: 596
8c Maas G. Angew. Chem. 2009; 121: 8332

9 For uniformity in the names of the targeted compounds (2-vinyldiazocarbonyl compounds) and their precursors (allylcarbonyl compounds), for the latter we use the term ‘vinyl’ instead of ‘allyl’ as recommended by the IUPAC rules.

10a Baum JS, Shook DA, Davies HM. L, Smith HD. Synth. Commun. 1987; 17: 1709
10b Davies HM. L, Saikali E, Clark TJ, Chee EH. Tetrahedron Lett. 1990; 31: 6299
10c Nikolaev VA, Kantin GP, Utkin PYu. Russ. J. Org. Chem. 1994; 30: 1354
10d Nikolaev VA, Kantin GP. Russ. J. Org. Chem. 2000; 36: 486

11a Guillaume M, Janousek Z, Viehe HG. Synthesis 1995; 920
11b Poschenrieder H, Stachel H. J. Heterocycl. Chem. 1995; 32: 1457
11c Zakharova VM, Hennig L, Nikolaev VA. Synthesis 2005; 2871
11d Galiullina SV, Zakharova VM, Kantin GP, Nikolaev VA. Russ. J. Org. Chem. 2007; 43: 607

For selected examples, see:

12a Lohaus G, Friedrich W, Jeschke JP. Chem. Ber. 1967; 100: 658
12b McIntosh CL, Chapman OL. J. Am. Chem. Soc. 1973; 95: 247
12c Alkony I. Chem. Ber. 1965; 98: 3099
12d Apparao S, Datta A, Ila H, Junjappa H. Synthesis 1985; 169
12e Guandalinia L, Deia S, Gualtieria F, Romanellia MN, Scapecchia S, Teodoria E, Varani K. Helv. Chim. Acta 2002; 85: 96
12f Chen L, Huang L, Zhang P. J. Org. Chem. 2003; 68: 5925

13 Mawaziny S, Lakani AM. Chim. Chron. 1996; 25: 215
14 Cherry K, Parrain JL, Thibonnet J, Duchene A, Abarbri M. J. Org. Chem. 2005; 70: 6669

15a Bestman HJ, Kratzer O. Chem. Ber. 1962; 95: 1894
15b Johnson AW, LaCount RB. Tetrahedron 1960; 9: 130

16 Lombardo L, Mander LN. Synthesis 1980; 368
17 Weygand F, Schwenke W, Bestmann HJ. Angew. Chem. 1958; 70: 506

18a Regitz M, Bartz W. Chem. Ber. 1970; 103: 1477
18b Popik VV, Nikolaev VA. J. Chem. Soc., Perkin Trans. 2 1993; 1971
18c Nikolaev VA, Ivanov AV, Shakhmin AA, Sieler J, Rodina LL. Tetrahedron Lett. 2012; 53: 3095

19 Peng C, Cheng J, Wang J. J. Am. Chem. Soc. 2007; 129: 8708

20a Nikolaev VA, Zhdanova OV, Korobitsyna IK. J. Org. Chem. USSR 1982; 18: 488
20b Padwa A, Kulkarni YS, Zhang Z. J. Org. Chem. 1990; 55: 4144
20c Davies HM. L, Hougland PW, Cantrell WR. Synth. Commun. 1992; 22: 971
20d Shi WF, Ma M, Wang JB. Chin. Chem. Lett. 2004; 15: 911

21a Davies HM. L, Hu B. Heterocycles 1993; 35: 385
21b Nadeau E, Ventura DL, Brekan JA, Davies HM. L. J. Org. Chem. 2010; 75: 1927

For reviews on the Horner–Wadsworth–Emmons reaction, see:

22a Boutagy J, Thomas R. Chem. Rev. 1974; 74: 87
22b Wadsworth WS. Org. React. 1977; 25: 73
22c Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863

For reviews on the Peterson olefination, see:

23a Van Staden LF, Gravestock D, Ager DJ. Chem. Soc. Rev. 2002; 31: 195
23b Kano N, Kawashima T. Modern Carbonyl Olefination . Takeda T. Wiley-VCH; Weinheim: 2004: 18
23c Korotchenko VN, Nenajdenko VG, Balenkova ES, Shastin AV. Russ. Chem. Rev. 2004; 73: 957
23d Ager DJ. Org. React. 1990; 38: 162

24 Sano S, Teranishi R, Nagao Y. Tetrahedron Lett. 2002; 43: 9183
25 Still WC, Gennari C. Tetrahedron Lett. 1983; 24: 4405

For reviews on the Still–Gennari reaction, see:

26a Motoyoshiya J. Trends Org. Chem. 1998; 7: 63
26b Edmonds M, Abell A. Modern Carbonyl Olefination . Takeda T. Wiley-VCH; Weinheim: 2004: 1

27 Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T. Tetrahedron Lett. 1984; 25: 2183
28 Gillies MB, Tonder JE, Tanner D, Norrby P. J. Org. Chem. 2002; 67: 7378

29a Wittig G, Schlosser M. Tetrahedron 1962; 18: 1023
29b Märkl G. Tetrahedron Lett. 1961; 807
29c Märkl G. Tetrahedron Lett. 1961; 811

30 Henrick CA, Willy WE, Baum JW, Baer TA, Garcia BA, Mastre TA, Chang SM. J. Org. Chem. 1975; 40: 1
31 Kuchkova KI, Morari AB, Vlad PF. Synthesis 1993; 1221

The starting methyl trifluorobutanoate 2f was prepared by a standard procedure.^32a It can contain a quantity of the ethyl trifluorobutanoate formed due to base-catalyzed transesterification during Claisen condensation.^32b In this case, the ethyl derivative impurity can also be present in the associated vinyl acetate 4f and further reaction products.

32a Burdon J, McLoughlim VC. R. Tetrahedron 1964; 20: 2163
32b Bender ML. J. Am. Chem. Soc. 1953; 75: 5986

33 Jenkinson SF, Booth KV, Estevez Reino AM, Horne G, Estevez RJ, Fleet GW. J. Tetrahedron: Asymmetry 2009; 20: 2357
34 Maas G, Muller A. Org. Lett. 1999; 1: 219

35a Marcoux D, Goudreau SR, Charette AB. J. Org. Chem. 2009; 74: 8939
35b Bestmann HJ, Kolm H. Chem. Ber. 1963; 96: 1948
35c Padwa A, Marcus M, Weingarten MD. Tetrahedron 1997; 53: 2371

Supplementary Material

Supporting Information