Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(5): 711-714
DOI: 10.1055/s-0030-1258414
DOI: 10.1055/s-0030-1258414
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A New Synthetic Protocol for the Preparation of Carbodiimides Using a Hypervalent Iodine(III) Reagent
Further Information
Received
15 November 2010
Publication Date:
17 January 2011 (online)
Publication History
Publication Date:
17 January 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201105/lookinside/thumbnails/10.1055-s-0030-1258414-1.jpg)
Abstract
A new, simple, and efficient preparation of symmetrical and unsymmetrical carbodiimides from the corresponding thioureas via dehydrosulfurization using a hypervalent iodine(III) reagent is described. The oxidation afforded carbodiimides in excellent yields and high selectivity. A possible mechanism for the transformation is proposed.
Key words
desulfurization - hypervalent iodine - oxidations - carbodiimides - catalysis
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Khorana HG. Chem. Rev. 1953, 53: 145 -
1b
Kurzer F.Douraghi-Zadeh K. Chem. Rev. 1967, 67: 107 -
1c
Williams A.Ibrahim IT. Chem. Rev. 1981, 81: 589 -
1d
Mikolajczyk M.Kielbasinski P. Tetrahedron 1981, 37: 233 -
2a
Ulrich H.Sayigh AAR. Angew. Chem., Int. Ed. Engl. 1966, 5: 704 -
2b
Kim S.Yi KY. Tetrahedron Lett. 1986, 27: 1925 -
2c
Kim S.Yi KY. J. Org. Chem. 1986, 51: 2613 -
2d
Isobe T.Ishikawa T. J. Org. Chem. 1999, 64: 6984 -
3a
Stevens CL.Singhal GH.Ash AB. J. Org. Chem. 1967, 32: 2895 -
3b
Hessel ET.Jones WD. Organometallics 1992, 11: 1496 -
3c
Schlama T.Gouverneur V.Mioskowski C. Tetrahedron Lett. 1996, 37: 7047 -
3d
Fell JB.Coppola GM. Synth. Commun. 1995, 25: 43 -
3e
Zhang M.Vedantham P.Flynn DL.Hanson PR. J. Org. Chem. 2004, 69: 8340 -
4a
Deeming AJ.Hardcastle K.Fuchita Y.Henrick K.McPartlin M. J. Chem. Soc., Dalton Trans. 1986, 2259 -
4b
Bryan JC.Rheingold AL.Geib SJ.Mayer JM. J. Am. Chem. Soc. 1987, 109: 2825 -
4c
Tang J.Mohan T.Verkade JG. J. Org. Chem. 1994, 59: 4931 -
4d
Barbaro G.Battaglia A.Giorgianni P.Guerrini A.Scconi G. J. Org. Chem. 1995, 60: 6032 -
4e
Rahman AKF.Nicholas KM. Tetrahedron Lett. 2007, 48: 6002 -
5a
Ito Y.Hirao T.Saegusa T. J. Org. Chem. 1975, 40: 2981 -
5b
Pri-Bar I.Schwartz J. Chem. Commun. 1997, 347 - 6
Ali AR.Ghosh H.Patel BK. Tetrahedron Lett. 2010, 51: 1019 -
7a
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997. -
7b
Hypervalent
Iodine Chemistry
Wirth T. Springer; Berlin: 2003. -
7c
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 -
7d
Varvoglis A. Tetrahedron 1997, 53: 1179 -
7e
Wirth T.Hirt UH. Synthesis 1999, 1271 -
7f
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
7g
Tohma H.Kita Y. Adv. Synth. Catal. 2004, 346: 111 -
7h
Koser GF. Adv. Heterocycl. Chem. 2004, 86: 225 -
7i
Moriarty RM. J. Org. Chem. 2005, 70: 2893 -
7j
Wirth T. Angew. Chem. Int. Ed. 2005, 44: 3656 -
7k
Ladziata U.Zhdankin VV. ARKIVOC 2006, (ix): 26 -
7l
Ochiai M. Chem. Rec. 2007, 7: 12 -
7m
Kita Y.Fujioka H. Pure Appl. Chem. 2007, 79: 701 -
7n
Zhdankin VV.Stang PJ. Chem. Rev. 2008, 108: 5299 -
7o
Ochiai M.Miyamoto K. Eur. J. Org. Chem. 2008, 4229 -
7p
Zhdankin VV. ARKIVOC 2009, (i): 1 -
7q
Dohi T.Kita Y. Chem. Commun. 2009, 2073 -
7r
Uyanik M.Ishihara K. Chem. Commun. 2009, 2086 -
7s
Uyanik M.Okamoto H.Yasui T.Ishihara K. Science 2010, 328: 1376 - 8
Singh CB.Ghosh H.Murru S.Patel BK. J. Org. Chem. 2008, 73: 2924 - 9
Ghosh H.Yella R.Nath J.Patel BK. Eur. J. Org. Chem. 2008, 6189 -
10a
Zhu C.Ji L.Wei Y. Synthesis 2010, 3121 -
10b
Zhu C.Ji L.Wei Y. Catal. Commun. 2010, 11: 1017 -
10c
Zhu C.Sun C.Wei Y. Synthesis 2010, 4235 -
10d
Zhu C.Ji L.Zhang Q.Wei Y. Can. J. Chem. 2010, 88: 362 -
10e
Zhu C.Ji L.Wei Y. Monatsh. Chem. 2010, 141: 327 -
10f
Zhu C.Wei Y.Ji L. Synth. Commun. 2010, 40: 2057 -
11a
Yamamoto Y.Togo H. Synlett 2006, 798 -
11b
Akiike J.Yamamoto Y.Togo H. Synlett 2007, 2168 -
11c
Yamamoto Y.Kawano Y.Toy PH.Togo H. Tetrahedron 2007, 63: 4680 -
12a
Stang PJ. Angew. Chem., Int. Ed. Engl. 1992, 31: 274 -
12b
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 -
13a
Ramadas K.Srinivasan N.Janarthanan N. Tetrahedron Lett. 1993, 34: 6447 -
13b
Novák L.Hanania M.Kovács P.Kovács CE.Kolonits P.Szántay C. Synth. Commun. 1999, 29: 1757 -
13c
Bollini M.Casal JJ.Alvarez DE.Boiani L.González M.Cerecetto H.Bruno AM. Bioorg. Med. Chem. 2009, 17: 1437