References
Recent reviews:
1a
Tavener SJ.
Clark JH.
J. Fluorine Chem.
2003,
123:
31
1b
Zhang W.
Tetrahedron
2003,
59:
4475
1c
Pozzi G.
Shepperson I.
Coord. Chem. Rev.
2003,
242:
115
1d
Yoshida J.
Itami K.
Chem. Rev.
2002,
102:
3693
1e
Dobbs AP.
Kimberley MR.
J. Fluorine Chem.
2002,
118:
3
1f
Curran DP.
Pure Appl. Chem.
2000,
72:
1649
1g
Curran DP. In Stimulating Concepts in Chemistry
Stoddard F.
Reinhoudt D.
Shibasaki M.
Wiley-VCH;
New York:
2000.
p.25-37
1h
de Wolf E.
van Koten G.
Deelman B.-J.
Chem. Soc. Rev.
1999,
28:
37
1i
Barthel-Rosa LP.
Gladysz JA.
Coord. Chem. Rev.
1999,
190-192:
587
1j
Betzemeier B.
Knochel P.
Top. Curr. Chem.
1999,
206:
61
1k
Fish RH.
Chem. Eur. J.
1999,
5:
1677
1l
Cavazzini M.
Montanari F.
Pozzi G.
Quici S.
J. Fluorine Chem.
1999,
94:
183
1m
Curran DP.
Angew. Chem. Int. Ed.
1998,
37:
1174
1n
Horváth IT.
Acc. Chem. Res.
1998,
31:
641
1o A collection of articles can be found in a special issue on Fluorous Chemistry, Tetrahedron Gladysz, J. A.; Curran, D. P., Eds. 2002, 58, 3823-4131.
2 A valuable reference will be available soon:
Handbook of Fluorous Chemistry
Gladysz JA.
Curran DP.
Horváth IT.
Wiley-VCH;
Weinheim:
2004.
p.in press
3a
Cavazzini M.
Quici S.
Pozzi G.
Tetrahedron
2002,
58:
3943
3b
Curran DP.
Synlett
2001,
1488
3c
Curran DP.
Luo Z.
J. Am. Chem. Soc.
1999,
121:
9069
3d
Kainz S.
Luo Z.
Curran DP.
Leitner W.
Synthesis
1998,
1425
4a
Nakamura H.
Usui T.
Kuroda H.
Ryu I.
Matsubara H.
Yasuda S.
Curran DP.
Org. Lett.
2003,
5:
1167
4b
Ryu I.
Matsubara H.
Yasuda S.
Nakamura H.
Curran DP.
J. Am. Chem. Soc.
2002,
124:
12946
4c
Luo Z.
Swaleh SM.
Theil F.
Curran DP.
Org. Lett.
2002,
4:
2585
4d
Nakamura H.
Linclau B.
Curran DP.
J. Am. Chem. Soc.
2001,
123:
10119
5
Isihara K.
Kondo S.
Yamamoto H.
Synlett
2001,
1371
6a
Wende M.
Gladysz JA.
J. Am. Chem. Soc.
2003,
125:
5861
6b
Wende M.
Meier R.
Gladysz JA.
J. Am. Chem. Soc.
2001,
123:
11490
7a
Dandapani S.
Curran DP.
Tetrahedron
2002,
58:
3855
7b
Dobbs AP.
McGregor-Johnson C.
Tetrahedron Lett.
2002,
43:
2807
7c
Rábai J.
Szabó D.
Borbás EK.
Kövesi I.
Kövesdi I.
Csámpai A.
Gömöry Á.
Pashinnik VE.
Shermolovich YG.
J. Fluorine Chem.
2002,
114:
199
8 Our work: Markowicz MW.
Dembinski R.
Org. Lett.
2002,
4:
3785
9
Crich D.
Neelamkavil S.
J. Am. Chem. Soc.
2001,
123:
7449
10
Hao X.
Yamazaki O.
Yoshida A.
Nishikido J.
Tetrahedron Lett.
2003,
44:
4977
11
Barrett AGM.
Braddock DC.
Catterick D.
Chadwick D.
Henschke JP.
McKinnell RM.
Synlett
2000,
847
12a
Vallin KSA.
Zhang Q.
Larhed M.
Curran DP.
Hallberg A.
J. Org. Chem.
2003,
68:
6639
12b
Moineau J.
Pozzi G.
Quici S.
Sinou D.
Tetrahedron Lett.
1999,
40:
7683
13
Tzschucke CC.
Markert C.
Glatz H.
Bannwarth W.
Angew. Chem. Int. Ed.
2002,
41:
4500
14
Markert C.
Bannwarth W.
Helv. Chim. Acta
2002,
85:
1877
15a
Hoshino M.
Degenkolb P.
Curran DP.
J. Org. Chem.
1997,
62:
8341
15b
Curran DP.
Hoshino M.
J. Org. Chem.
1996,
61:
6480
16
Chen D.
Qing F.
Huang Y.
Org. Lett.
2002,
4:
1003
Selected recent papers/reviews:
17a
Shangguan N.
Katukojvala S.
Greenberg R.
Williams LJ.
J. Am. Chem. Soc.
2003,
125:
7754
17b
Carpino LA.
Ghassemi S.
Ionescu D.
Ismail M.
Sadat-Aalaee D.
Truran GA.
Mansour EME.
Siwruk GA.
Eynon JS.
Morgan B.
Org. Process Res. Dev.
2003,
7:
28
17c
Albericio F.
Chinchilla R.
Dodsworth DJ.
Najera C.
Org. Prep. Proced. Int.
2001,
33:
205
18
Luo Z.
Williams J.
Read RW.
Curran DP.
J. Org. Chem.
2001,
66:
4261
19a
Filippov DV.
van Zoelen DJ.
Oldfield SP.
van der Marel GA.
Overkleeft HS.
Drijfhout JW.
van Boom JH.
Tetrahedron Lett.
2002,
43:
7809
19b
Curran DP.
Amatore M.
Guthrie D.
Campbell M.
Go E.
Luo Z.
J. Org. Chem.
2003,
68:
4643
Recent representative examples of applications of chloro-1,3,5-triazine:
20a
De Luca L.
Giacomelli G.
Porcheddu A.
Org. Lett.
2002,
4:
553
20b
De Luca L.
Giacomelli G.
Porcheddu A.
Org. Lett.
2001,
3:
3041
20c
Rayle HL.
Fellmeth L.
Org. Process Res. Dev.
1999,
3:
172
20d
Lee PH.
Sawan SP.
Modrusan Z.
Arnold LJ.
Reynolds MA.
Bioconjugate Chem.
2002,
13:
97
20e For polystyrene-supported chlorotriazine couplings, see: Bork JT.
Lee JW.
Chang Y.-T.
Tetrahedron Lett.
2003,
44:
6141
20f See also: Masala S.
Taddei M.
Org. Lett.
1999,
1:
1355
21a
Giacomelli G.
Porcheddu A.
Salaris M.
Org. Lett.
2003,
5:
2715
21b
De Luca L.
Giacomelli G.
Porcheddu A.
J. Org. Chem.
2002,
67:
6272
22a
Carpino LA.
Beyermann M.
Wenschuh H.
Bienert M.
Acc. Chem. Res.
1996,
29:
268
22b
Carpino LA.
Mansour EME.
Sadat-Aalaee D.
J. Org. Chem.
1991,
56:
2611
22c
Carpino LA.
Sadat-Aalaee D.
Chao HG.
DeSelms RH.
J. Am. Chem. Soc.
1990,
112:
9651
23
Carpino LA.
Ionescu D.
El-Faham A.
Beyermann M.
Henklein P.
Hanay C.
Wenschuh H.
Bienert M.
Org. Lett.
2003,
5:
975
24
Kamiñski ZJ.
Biopolymers
2000,
55:
140
25a
Cronin JS.
Ginah FO.
Murray AR.
Copp JD.
Synth. Commun.
1996,
26:
3491
25b
Weber AJM.
Huysmans WGB.
Mijs WJ.
Bovée WMMJ.
Smidt J.
Vriend J.
Recl. Trav. Chim. Pays-Bas
1978,
97:
107
25c
Dudley JR.
Thurston JT.
Schaefer FC.
Holm-Hansen D.
Hull CJ.
Adams P.
J. Am. Chem. Soc.
1951,
73:
2986
26a
Bandgar BP.
Pandit SS.
Tetrahedron Lett.
2003,
44:
3855
26b
Bandgar BP.
Pandit SS.
Tetrahedron Lett.
2003,
44:
2331
26c
De Luca L.
Giacomelli G.
Taddei M.
J. Org. Chem.
2001,
66:
2534
26d
De Luca L.
Giacomelli G.
Porcheddu A.
Org. Lett.
2001,
3:
1519
26e
Kunishima M.
Yoshimura K.
Morigaki H.
Kawamata R.
Terao K.
Tani S.
J. Am. Chem. Soc.
2001,
123:
10760
26f
Pontikis R.
Dolle V.
Guillaumel J.
Dechaux E.
Note R.
Nguyen CH.
Legraverend M.
Bisagni E.
Aubertin A.-M.
Grierson DS.
Monneret C.
J. Med. Chem.
2000,
43:
1927
27
Kamiñska JE.
Kamiñski ZJ.
Góra J.
Synthesis
1999,
593
28
Kamiñski ZJ.
Paneth P.
Rudzi ñski J.
J. Org. Chem.
1998,
63:
4238
29
Kamiñski ZJ.
Tetrahedron Lett.
1985,
26:
2901
30
Garrett C.
Jiang X.
Prasad K.
Repi è O.
Tetrahedron Lett.
2002,
43:
4161
31
Kamiñski ZJ.
Synthesis
1987,
917
See, for example:
32a
Inai Y.
Ousaka N.
Okabe T.
J. Am. Chem. Soc.
2003,
125:
8151
32b
Venkatraman J.
Shankaramma SC.
Balaram P.
Chem. Rev.
2001,
101:
3131
32c
Obrecht D.
Abrecht C.
Altorfer M.
Bohdal U.
Grieder A.
Kleber M.
Pfyffer P.
Müller K.
Helv. Chim. Acta
1996,
79:
1315
32d
Di Blasio B.
Pavone V.
Saviano M.
Lombardi A.
Nastri F.
Pedone C.
Benedetti E.
Crisma M.
Anzolin M.
Toniolo C.
J. Am. Chem. Soc.
1992,
114:
6273
32e
Toniolo C.
Benedetti E.
Macromolecules
1991,
24:
4004
32f
Hruby VJ.
Al-Obeidi F.
Kazmierski W.
Biochem. J.
1990,
268:
249
32g
Toniolo C.
Benedetti E.
ISI Atlas Sci. Biochem.
1988,
1:
225
33a
Santagada V.
Fiorino F.
Perissutti E.
Severino B.
De Filippis V.
Vivenzio B.
Caliendo G.
Tetrahedron Lett.
2001,
42:
5171
33b
Leibfritz D.
Haupt E.
Dubischar N.
Lachmann H.
Oekonomopulos R.
Jung G.
Tetrahedron
1982,
38:
2165
33c
Balasubramanian TM.
Kendrick NCE.
Taylor M.
Marshall GR.
Hall JE.
Vodyanoy I.
Reusser F.
J. Am. Chem. Soc.
1981,
103:
6127
34
Frérot E.
Coste J.
Pantaloni A.
Dufour M.-N.
Jouin P.
Tetrahedron
1991,
47:
259
35
Kamiñski ZJ.
Kolesiñska B.
Kamiñska JE.
Góra J.
J. Org. Chem.
2001,
66:
6276
36
Studer A.
Jeger P.
Wipf P.
Curran DP.
J. Org. Chem.
1997,
62:
2917
37
Herrera V.
de Rege PJF.
Horváth IT.
Le Husebo T.
Hughes RP.
Inorg. Chem. Commun.
1998,
1:
197
38a
Breed LW.
Burton WH.
Kraebel CM.
J. Org. Chem.
1965,
30:
3224
38b
Breed LW.
Burton WH.
Kraebel CM.
J. Chem. Eng. Data
1965,
10:
384
38c Carignano G, Russo A, Savarino P, Baratta P, and Visca M. inventors; EP 1033368.
; Chem. Abstr.
2000, 133, 239311
39 Hoentjen G, de Graaf SAG, Bijkerk AK, and de Jonge CRHI. inventors; US Patent 4204060.
; Chem. Abstr. 1981, 94, 15777y
40 The term ‘hydroxytriazine’ is used for the triazine by-product. However, energetically favored hydroxyimino-amide equilibrium is attributed to excellent leaving group properties.
41a
Kunishima M.
Kawachi C.
Hioki K.
Terao K.
Tani S.
Tetrahedron
2001,
57:
1551
41b
Falchi A.
Giacomelli G.
Porcheddu A.
Taddei M.
Synlett
2000,
275
41c
Kunishima M.
Kawachi C.
Morita J.
Terao K.
Iwasaki F.
Tani S.
Tetrahedron
1999,
55:
13159
41d
Kunishima M.
Morita J.
Kawachi C.
Iwasaki F.
Terao K.
Tani S.
Synlett
1999,
1255
41e
Kunishima M.
Kawachi C.
Iwasaki F.
Terao K.
Tani S.
Tetrahedron Lett.
1999,
40:
5327
42
Chiriac CI.
Onciu M.
Tibirna M.
Tanasa F.-M.
Truşcan I.
Ropot R.
Rev. Roum. Chim.
1998,
43:
31
43
Jones JH.
Liberek B.
Young GT.
J. Chem. Soc. C
1967,
2371
Lee S.
Kanmera T.
Ayoagi H.
Izumiya N.
Int. J. Pept. Protein Res.
1979,
13:
207
Lübke K.
Schröder E.
Schmichen R.
Gibian H.
Liebigs Ann. Chem.
1964,
679:
195
45
Kamiński ZJ.
Sci. Bull. Tech. Univ. Łódź
1996,
763:
3 ; in Polish
46
Kamiński ZJ.
Int. J. Pept. Protein Res.
1994,
43:
312
47
Visser S.
Roeloffs J.
Kerling KET.
Havinga E.
Recl. Trav. Chim. Pays-Bas
1968,
87:
559
48 A flask was charged with 1 (0.506 g, 0.500 mmol), 2c (0.111 g, 0.497 mmol), 3c·HCl (0.070 g, 0.50 mmol), and THF (10 mL). The mixture was cooled to 0 °C and a solution of NMM in THF (10% v/v, 1.15 mL, 1.05 mmol) was added dropwise. The mixture was stirred for 2 h at 0 °C. The ice bath was removed and the mixture was allowed to reach r.t. while stirring for 14 h. Work-up similar to General Procedure gave 4c as a white solid (0.086 g, 56%).
49a
Tonelli AE.
J. Am. Chem. Soc.
1973,
95:
5946
49b
Breznik M.
Grdadolnik SG.
Giester G.
Leban I.
Kikelj D.
J. Org. Chem.
2001,
66:
7044
49c
Fischer S.
Dunbrack RL.
Karplus M.
J. Am. Chem. Soc.
1994,
116:
11931
49d For detailed NMR conformational studies of proline peptides, see for example: Madalengoitia JS.
J. Am. Chem. Soc.
2000,
122:
4986
50
Ben-Ishai D.
Berger A.
J. Org. Chem.
1952,
17:
1564
51 4-{4,6-Bis[(heptadecafluorononyl)oxy]-1,3,5-triazin-2-yl}-4-methylmorpholinium chloride (5) was isolated by filtration and characterized by 1H NMR spectroscopy. 1H NMR (acetone-d
6): δ = 5.20 (t, J = 13.8 Hz, 4 H, CF2CH2O), 3.91 (t, J = 4.8 Hz, 4 H, NCH2CH
2O), 3.76 (t, J = 4.8 Hz, 4 H, NCH
2CH2O), 2.12 (s, 3 H, CH3).
52 Vibration assignments for the C3N3 ring (D3h;E¢ in-plane stretching; A2¢¢: out-of-plane bending) based on: Herman TS.
Appl. Spectrosc.
1966,
20:
159
53 Peak assigned to traces of 2,4,6,-tris[(heptadecafluorononyl)oxy]-1,3,5-triazine.
54
Hoogwater DA.
Peereboom M.
Tetrahedron
1990,
46:
5325
55 ‘L’ and ‘R’ denote ‘left’ and ‘right’ amino acid fragments for the Cbz-Aaa- and Aaa-OMe fragments, where assignments were possible.
56 ‘*’ denotes the chemical shift for the minor isomer.
57
Okada Y.
Okinaka M.
Yagyu M.
Watabe K.
Sano K.
Kakiuchi Y.
Chem. Pharm. Bull.
1976,
24:
3081
58
Ipso signal was not observed.
