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Synthesis 2008(22): 3625-3632
DOI: 10.1055/s-0028-1083215
DOI: 10.1055/s-0028-1083215
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations
Further Information
Received
28 July 2008
Publication Date:
10 November 2008 (online)
Publication History
Publication Date:
10 November 2008 (online)
Abstract
o-Benzenedisulfonimide turns out to be a highly efficient Brønsted acid catalyst for the acylation of a number of alcohols, phenols, and thiols under a metal- and solvent-free procedure; reaction conditions are mild and yields very good. After the workup, the catalyst can be easily recovered and purified, ready to be reused, with economic and ecological advantages.
Key words
o-benzenedisulfonimide - acid catalysis - recyclable catalyst - acylation reaction
-
1a
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: John Wiley & Sons; New York: 1999. -
1b
Larock RC. Comprehensive Organic Transformations 2nd ed.: Wiley-VCH; New York: 1999. -
1c
Mulzer J. In Comprehensive Organic Synthesis 1st ed., Vol. 6:Trost BM.Fleming I. Pergamon; New York: 1991. Chap. 2. p.323-333 - 2
Chandra KL.Saravanan P.Singh RK.Singh VK. Tetrahedron 2002, 58: 1369 - 3
Chakraborti AK. . J. Org. Chem. 2006, 71: 5785 - 4
Shirini F.Zolfigol MA.Mallakpour B. Int. J. Chem. Sci. 2003, 1: 53 - 5
Kamal A.Khan MNA.Reddy KS.Srikanth YVV.Krishnaji T. Tetrahedron Lett. 2007, 48: 3813 - 6
Ishihara K.Kubota M.Kurihara H.Yamamoto H. J. Org. Chem. 1996, 61: 4560 -
7a LiOTf:
Karimi B.Maleki J. J. Org. Chem. 2003, 68: 4951 -
7b LiClO4:
Nakae Y.Kusaki I.Sato T. Synlett 2001, 1584 -
7c LiCl:
Sabitha G.Reddy BVS.Srividya R.Yadav JS. Synth. Commun. 1999, 29: 2311 -
8a
Peng ZH.Orita A.An D.Otera J. Tetrahedron Lett. 2005, 46: 3187 -
8b
Orita A.Sakamoto K.Hamada Y.Mitsutome A.Otera J. Tetrahedron 1999, 55: 2899 -
8c
Satam JR.Gawande MB.Deshpande SS.Jayaram RV. Synth. Commun. 2007, 37: 3011 - 9
Procopio A.Dalpozzo R.De Nino A.Maiuolo L.Russo B.Sindona G. Adv. Synth. Catal. 2004, 346: 1465 - 10
Dalpozzo R.De Nino A.Maiuolo L.Oliverio M.Procopio A.Russo B.Tocci A. Aust. J. Chem. 2007, 60: 75 - 11
Bhattacharya AK.Diallo MA.Ganesh KN. Synth. Commun. 2008, 38: 1518 -
12a
Yadav JS.Narsaiah AV.Basak AK.Goud PR.Sreenu D.Nagaiah K. J. Mol. Catal. A: Chem. 2006, 255: 78 -
12b
Yadav JS.Narsaiah AV.Reddy BV.Basak AK.Nagaiah K. J. Mol. Catal. A: Chem. 2005, 230: 107 - 13
Chakraborti AK.Gulhane R. Tetrahedron Lett. 2003, 44: 6749 - 14
Chandrasekhar S.Ramachander T.Takhi M. Tetrahedron Lett. 1998, 39: 3263 - 15
Iqbal J.Srivastava RR. J. Org. Chem. 1992, 57: 2001 -
16a
Moghadam M.Tangestaninejad S.Mirkhani V.Mohammadpoor-Baltork I.Taghavi SA. J. Mol. Catal. A: Chem. 2007, 274: 217 -
16b
Moghadam M.Tangestaninejad S.Mirkhani V.Mohammadpoor-Baltork I.Shaibani R. J. Mol. Catal. A: Chem. 2004, 219: 73 -
16c
Tangestaninejad S.Habibi MH.Mirkhani V.Moghadam M. Synth. Commun. 2002, 32: 1337 - 17
Reddy TS.Narasimhulu M.Suryakiran N.Mahesh KC.Ashalatha K.Venkateswarlu Y. Tetrahedron Lett. 2006, 47: 6825 - 18
Parac-Vogt TN.Deleersnyder K.Binnemans K. Eur. J. Org. Chem. 2005, 1810 -
19a CuSO4˙5H2O:
Heravi MM.Behbahani FK.Zadsirjan V.Oskooie HA. J. Braz. Chem. Soc. 2006, 17: 1045 -
19b Cu(ClO4)2:
Jeyakumar K.Chand DK. J. Mol. Catal. A: Chem. 2006, 255: 275 -
19c
Chakraborti AK.Gulhane R. . Synthesis 2004, 111 -
19d Cu(OTf)2:
Saravanan P.Singh VK. Tetrahedron Lett. 1999, 40: 2611 - 20
Chakraborti AK.Gulhane R. . Synlett 2003, 1805 -
21a
Kantam ML.Aziz K.Likhar PR. Catal. Commun. 2006, 7: 484 -
21b
Shirini F.Zolfigol MA.Safari A. J. Chem. Res., Synop. 2006, 154 -
21c
Shirini F.Zolfigol MA.Safari A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005, 44: 201 -
22a Ce(OTf)3:
Dalpozzo R.De Nino A.Maiuolo L.Procopio A.Nardi M.Bartoli G.Romeo R. Tetrahedron Lett. 2003, 44: 5621 -
22b CAN:
Khaja SD.Xue J. Lett. Org. Chem. 2006, 3: 554 -
22c Ammonium decatungstocerate(IV):
Mirkhani V.Tangestaninejad S.Moghadam M.Yadollahi B.Alipanah L. Monatsh. Chem. 2004, 135: 1257 - 23
Salavati-Niasari M.Hydarzadeh S.Amiri A.Salavati S. J. Mol. Catal. A: Chem. 2005, 231: 191 -
24a
Alleti R.Oh WS.Perambuduru M.Afrasiabi Z.Sinn E.Reddy VP. Green Chem. 2005, 7: 203 -
24b
Alleti R.Perambuduru M.Samantha S.Reddy VP. J. Mol. Catal. A: Chem. 2005, 226: 57 - 25
Shirini F.Zolfigol MA.Abedini M. Monatsh. Chem. 2004, 135: 279 - 26
Martinez-Pascual R.Vinas-Bravo O.Meza-Reyes S.Iglesias-Arteaga MA.Sandoval-Ramirez J. Synth. Commun. 2004, 34: 4591 - 27
Habibi MH.Tangestaninejad S.Mirkhani V.Yadollahi B. Synth. Commun. 2002, 32: 863 - 28
Mohammadpoor-Baltork I.Aliyan H.Khosropour AR. Tetrahedron 2001, 57: 5851 -
29a
Shirini F.Zolfigol MA.Khaleghi M. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178: 1999 -
29b
Procopiou PA.Baugh SPD.Flack SS.Inglis GGA. J. Org. Chem. 1998, 63: 2342 -
29c
Kumareswaran R.Gupta A.Vankar YD. Synth. Commun. 1997, 27: 277 -
30a
Cope AC.Herrich EC. Org. Synth. Coll. Vol. IV John Wiley & Sons; London: 1963. p.304 -
30b
Furuta K.Iwanaga K.Yamamoto H. Org. Synth. Coll. Vol. VIII John Wiley & Sons; London: 1993. p.141 - 31
Kadam ST.Kim SS. Synthesis 2008, 267 - 32
Tale RH.Adude RN. Tetrahedron Lett. 2006, 47: 7263 - 33
Jin TS.Ma YR.Zhang ZH.Li TS. Synth. Commun. 1998, 28: 3173 - 34
Li TS.Li AX. J. Chem. Soc., Perkin Trans. 1 1998, 1913 -
35a
Srivastava R.Venkatathri N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 888 -
35b
Bhaskar PM.Loganathan D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 892 -
35c
Heravi MM.Tajbakhsh M.Mohajerani B.Ghassemzadeh M. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999, 38: 859 -
35d
Ballini R.Bosica G.Carloni S.Ciaralli L.Maggi R.Sartori G. Tetrahedron Lett. 1998, 39: 6049 -
36a
Reddy BM.Sreekanth PM. Synth. Commun. 2002, 32: 2815 -
36b
Kumar P.Pandey RK.Bodas MS.Dongare MK. Synlett 2001, 206 -
36c
Curini M.Epifano F.Marcotullio MC.Rosati O.Rossi M. Synth. Commun. 2000, 30: 1319 - 37
Kumareswaran R.Pachamuthu K.Vankar YD. Synlett 2000, 1652 -
38a
Thakuria H.Borah BM.Das G. J. Mol. Catal. A: Chem. 2007, 274: 1 -
38b
Sarvari MH.Sharghi H. Tetrahedron 2005, 61: 10903 - 39
Ma YR.Jin TS.Whang ZH.Li TS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42: 1777 -
40a
Farhadi S.Taherimehr M. Catal. Commun. 2008, 9: 703 -
40b
Heravi MM.Behbahani FK.Bamoharram FF. ARKIVOC 2007, (xvi): 123 -
40c
Alizadeh MH.Kermani T.Tayebee R. Monatsh. Chem. 2007, 138: 165 -
40d
Heravi MM.Behbahani FK.Bamoharram FF. J. Mol. Catal. A: Chem. 2006, 253: 16 -
41a
Ratnam KJ.Reddy RS.Sekhar NS.Kantam AL.Figueras F. J. Mol. Catal. A: Chem. 2007, 276: 230 -
41b
Joseph JK.Jain SL.Sain B. J. Mol. Catal. A: Chem. 2007, 267: 108 -
42a
Das B.Thirupathi P. J. Mol. Catal. A: Chem. 2007, 269: 12 -
42b
Das B.Thirupath P.Kumar RA.Laxminarayana K. Adv. Synth. Catal. 2007, 349: 2677 -
42c
Eshghi H.Shafieyoon P. J. Chem. Res., Synop. 2004, 802 -
42d
Shirini F.Zolfigol MA.Mohammadi K. Bull. Korean Chem. Soc. 2004, 25: 325 -
42e
Jin TS.Xiao JC.Wang ZH.Li TS. J. Chem. Res., Synop. 2003, 412 -
42f
Chakraborti AK.Gulhane R. Tetrahedron Lett. 2003, 44: 3521 -
43a
Lee SG.Park JH. J. Mol. Catal. A: Chem. 2003, 194: 49 -
43b
Forsyth SA.MacFarlen DR.Thomson RJ.von Itzstein M. Chem. Commun. 2002, 714 -
43c
Gholap AR.Venkatesan K.Daniel T.Lahoti RJ.Srinivasan KV. Green Chem. 2003, 5: 693 -
44a
Zhang L.Luo Y.Fan RH.Wu J. Green Chem. 2007, 9: 1022 -
44b
Zolfigol MA.Khazael A.Choghamarani AG.Rostami A.Hajjami M. Catal. Commun. 2006, 7: 399 -
44c
Khazaei A.Rostami A.Tanbakouchian Z.Zinati Z. Catal. Commun. 2006, 7: 214 -
44d
Khazaei A.Rostami A.Tanbakouchian Z.Zinati Z. J. Braz. Chem. Soc. 2006, 17: 206 -
44e
Karimi B.Seradj H. Synlett 2001, 519 -
45a
Khan AT.Islam S.Majee A.Chattopadhyay T.Ghosh S. J. Mol. Catal. A: Chem. 2005, 239: 158 -
45b
Khan AT.Choudhury LH.Ghosh S. Eur. J. Org. Chem. 2005, 2782 -
46a
Mojtahedi MM.Abaee MS.Heravi MM.Behbahani FK. Monatsh. Chem. 2007, 138: 95 -
46b
Ranu BC.Dey SS.Hajra A. Green Chem. 2003, 5: 44 -
46c
Bangdar BP.Pasture SP.Kamble VT. Synth. Commun. 2001, 31: 2255 -
47a
Barbero M.Cadamuro S.Dughera S.Venturello P. Synthesis 2008, 1379 -
47b
Barbero M.Cadamuro S.Dughera S.Venturello P. Synlett 2007, 2209 - 48
Hollemann AF. Recl. Trav. Chim. Pays-Bas 1921, 40: 446 - 49
Hurtley WR.Smiles S. J. Chem. Soc. 1926, 1821 - 50
Hendrickson JB.Okano S.Bloom RK. J. Org. Chem. 1969, 34: 3434 - 51
Blaschette A.Jones PG.Hamann T.Näveke M. Z. Anorg. Allg. Chem. 1993, 619: 912 - 52
Davis FA.Sundarababu G.Qi H. Org. Prep. Proced. Int. 1998, 30: 107 - 53
Barbero M.Degani I.Fochi R.Regondi V. Gazz. Chim. Ital. 1986, 116: 165 - 54
Sørbye K.Tautermann C.Carlsen P.Fiksdahl A. Tetrahedron: Asymmetry 1998, 9: 681 - 55
Karino H,Goda H,Sakamoto J.-I,Yoshida K, andNishiguchi H. inventors; WO 9633167. ; Chem. Abstr. 1997, 126, 18657 - 56
Firouzabadi H.Iranpoor N.Hazarkhani H.Karimi B. Synth. Commun. 2003, 33: 3653 -
57a
Barbero M,Degani I,Fochi R, andPerracino P. inventors; WO 9839312. ; Chem. Abstr. 1998, 129, 244942 -
57b
Barbero M.Crisma M.Degani I.Fochi R.Perracino P. Synthesis 1998, 1171 - 58
Stoughton RW. J. Am. Chem. Soc. 1935, 57: 202 - 59
Cai X.Sakamoto M.Yamaji M.Fujitsuka M.Majima T. Chem. Eur. J. 2007, 13: 3142 - 60
González-Núñez ME.Mello R.Olmos A.Asensio G. J. Org. Chem. 2005, 70: 10879 - 61
Eames J.Khanom H. Molecules 2004, 9: 266 - 62
McNulty J.Nair JJ.Cheekoori S.Larichev V.Capretta A.Robertson AJ. Chem. Eur. J. 2006, 12: 9314 - 63
Contento M.Manescalchi F.Mussatto MC.Cainelli G. Synthesis 1981, 302 - 64
Alnajjar MS.Garrossian MS.Autrey ST.Ferris KF.Franz JA. J. Phys. Chem. C 1992, 96: 7037 - 65
Dhimitruka I.SantaLucia J. Org. Lett. 2006, 8: 47 - 66
Crimmin MR.Barrett AGM.Hill MS.Procopiu PA. Org. Lett. 2007, 9: 331 - 67
Cluzeau J.Capdevielle P.Cossy J. Tetrahedron Lett. 2005, 46: 6945 - 68
Fuchs S.Berl V.Lepoittevin J.-P. Eur. J. Org. Chem. 2007, 1145 - 69
Sydnes LK.Sandberg M. Tetrahedron 1997, 53: 12679 - 70
Gonzales N.Martin I.Chuchani G. J. Phys. Chem. 1985, 89: 1314 - 71
Aldrich TB. J. Am. Chem. Soc. 1920, 42: 1502