Abstract
Photoinduced electron transfer reaction between N -tosyl amides and 2-phenyl-N ,N ′-dimethylbenzimidazoline (PDMBI) provides an efficient approach for the desulfonylation of N -tosyl amides.
Key words
N -tosyl amides - deprotection - photoinduced electron transfer - 2-phenyl-N ,N ′-dimethylbenzimidazoline
References
1a Greene TW.
Wuts PGM.
Protective Groups in Organic Synthesis
3rd ed.:
Wiley-Interscience;
New York:
1999.
1b Kocienski PJ.
Protecting Groups
Thieme;
New York:
1994.
2a Nagashima H.
Ozaki N.
Washiyama M.
Itoh K.
Tetrahedron Lett.
1985,
26:
657
2b Alonso E.
Ramón DJ.
Yus M.
Tetrahedron
1997,
53:
14355
3 Roemmele RC.
Rapaport H.
J. Org. Chem.
1988,
53:
2367
4 Knowles H.
Parsons AF.
Pettifer RM.
Synlett
1997,
271
5 Nyasse B.
Grehn L.
Ragnarsson U.
Chem. Commun.
1997,
1017
6 Yasuhara A.
Sakamoto T.
Tetrahedron Lett.
1998,
39:
595
7 Sabitha G.
Reddy BVS.
Abraham S.
Yadav JS.
Tetrahedron Lett.
1999,
40:
1569
8a Parsons AF.
Pettifer RM.
Tetrahedron Lett.
1996,
37:
1667
8b Knowles HS.
Parsons AF.
Pettifer RM.
Rickling S.
Tetrahedron
2000,
56:
979
9a Pete JP.
Portella C.
J. Chem. Res., Miniprint
1979,
209
9b Li C.
Fuchs PL.
Tetrahedron Lett.
1993,
34:
1855
9c Hamada T.
Nishida A.
Yonemitsu O.
J. Am. Chem. Soc.
1986,
108:
140
9d Art JF.
Kestemont JP.
Soumillion JP.
Tetrahedron Lett.
1991,
32:
1425
10a Chikashita H.
Ide H.
Itoh K.
J. Org. Chem.
1986,
51:
5400
10b Chikashita H.
Itoh K.
Bull. Chem. Soc. Jpn.
1986,
59:
1747
10c Chen J.
Tanner DD.
J. Org. Chem.
1988,
53:
3897
10d Tanner DD.
Chen JJ.
J. Org. Chem.
1989,
54:
3842
10e Tanner DD.
Chen JJ.
Chen L.
Luelo C.
J. Am. Chem. Soc.
1991,
113:
8074
10f Tanner DD.
Chen JJ.
J. Org. Chem.
1992,
57:
662
10g Lee I.-SH.
Jeoung EH.
Kreevoy MM.
J. Am. Chem. Soc.
2001,
123:
7492
10h Hasegawa E.
Yoneoka A.
Suzuki K.
Kato T.
Kitazume T.
Yanagi K.
Tetrahedron
1999,
55:
12957
10i Hasegawa E.
Chiba N.
Nakajima A.
Suzuki K.
Yoneoka A.
Iwaya K.
Synthesis
2001,
1248
10j Hasegawa E.
Takizawa S.
Iwaya K.
Kurokawa M.
Chiba N.
Yamamichi K.
Chem. Commun.
2002,
1966
10k Hasegawa E.
Chiba N.
Takahashi T.
Takizawa S.
Kitayama T.
Suzuki T.
Chem. Lett.
2004,
33:
18
11 Jin MZ.
Yang L.
Wu LM.
Liu YC.
Liu Z.-L.
Chin. Chem. Lett.
2001,
12:
307
12 Casadei MA.
Gessner A.
Inesi A.
Jugelt W.
Moracci FM.
J. Chem. Soc., Perkin Trans. 1
1992,
2001
13 For example 2b : MS (EI): m/z (rel. int.) = 191 (13), 149 (32), 106 (48), 91 (100), 77 (14). 1 Η ΝMR (300 MHz, CDCl3 ): δ = 7.26 m (5 H), 6.42 (br s, 1 H), 4.35 (d, J = 5.7 Hz, 2 H), 2.17 (t, J = 7.5 Hz, 2 H), 1.59 (quin, J = 7.5 Hz, 2 H), 1.28 (sext, J = 7.5 Hz, 2 H), 0.88 (t, J = 7.5 Hz, 3 H). 13 C NMR (75 MHz): δ = 173.2, 138.4, 128.4, 127.5, 127.2, 43.2, 36.2, 27.7, 22.3, 13.6.
14 Mella M.
Fagnoni M.
Freccero M.
Fasani E.
Albini A.
Chem. Soc. Rev.
1998,
27:
81
15a Maslak P.
Narvaez JN.
Angew. Chem., Int. Ed. Engl.
1990,
29:
283
15b Maslak P.
Kula J.
Chateauneuf JE.
J. Am. Chem. Soc.
1991,
113:
2304
