Abstract
The decarboxylative bromination of cinnamic acids using the hypervalent iodine reagent 2-iodoxybenzoic acid with tetrabutylammonium bromide is described, providing good to excellent yields of bromostyrenes. Bromostyrenes are useful coupling components in a wide range of transition metal-catalysed coupling reactions.
References
1.
Naskar D.
,
Chowdhury S.
, and
Roy S.
, Tetrahedron Lett. , 1998 , 39 , 699 .
2.
Naskar D.
, and
Roy S.
, Tetrahedron , 2000 , 56 , 1369 .
3.
Das J.P.
, and
Roy S.
, J. Org. Chem. , 2002 , 67 , 7861 .
4.
Chowdhury S.
, and
Roy S.
, Tetrahedron Lett , 1996 , 37 , 2623 .
5.
Sinha J.
,
Layek S.
,
Mandal G.C.
, and
Bhattacharjee M.
, Chem. Commun. , 2001 , 1916 .
6.
Roy S.C.
,
Guin C.
, and
Maiti G.
, Tetrahedron Lett , 2001 , 42 , 9253 .
7.
Kuang C.
,
Yang Q.
,
Senboku H.
, and
Tokuda M.
, Synthesis , 2005 , 1319 .
8.
Wang C.
,
Bao W.
, and
Zhang X.
, J. Chem. Res. , 2005 , 2005 , 617 .
9.
Telvekar V.N.
,
Arote N.D.
, and
Herlekar O.P.
, Synlett , 2005 , 2495 .
10.
Fursule R.A.
,
Patil P.O.
,
Shewale B.D.
,
Kosalge S.B.
,
Deshmukh P.K.
, and
Patil D.A.
, Chem. Pharm. Bull. , 2009 , 57 , 1243 .
11.
Graven A.
,
Joergensen K.A.
,
Dahl S.
, and
Stanczak A.
, J. Org. Chem. , 1994 , 59 , 3543 .
12.
Camps P.
,
Lukach A.E.
,
Pujol X.
, and
Vázquez S.
, Tetrahedron , 2000 , 56 , 2703 .
13.
Zhdankin V.V.
, J. Org. Chem. , 2011 , 76 , 1185 .
14.
Duschek A.
, and
Kirsch S.F.
, Angew. Chem. Int. Ed. , 2011 , 50 , 1524 .
15.
Satam V.
,
Harad A.
,
Rajule R.
, and
Pati H.
, Tetrahedron , 2010 , 66 , 7659 .
16.
Fontaine P.
,
Masson G.R.
, and
Zhu J.
, Org. Lett. , 2009 , 11 , 1555 .
17.
Fontaine P.
,
Chiaroni A.
,
Masson G.
, and
Zhu J.
, Org. Lett. , 2008 , 10 , 1509 .
18.
Bhalerao D.S.
,
Mahajan U.S.
,
Chaudhari K.H.
, and
Akamanchi K.G.
, J. Org. Chem. , 2006 , 72 , 662 .
19.
Zhdankin V.V.
,
Koposov A.Y.
,
Litvinov D.N.
,
Ferguson M.J.
,
McDonald R.
,
Luu T.
, and
Tykwinski R.R.
, J. Org. Chem. , 2005 , 70 , 6484 .
20.
Robert J.
,
Boeckman K.
,
Shao P.
, and
Mullins J.J.
, Organic Syntheses. Coll. Vol. , 2004 , 10 , 696 .
21.
Kuang C.
,
Senboku H.
, and
Tokuda M.
, Tetrahedron , 2002 , 58 , 1491 .
22.
Gao F.
, and
Hoveyda A.H.
, J. Am. Chem. Soc. , 2010 , 132 , 10961 .
23.
Bull J.A.
,
Mousseau J.J.
, and
Charette A.B.
, Organic Letters , 2008 , 10 , 5485 .
24.
Podgoršek A.
,
Jurisch M.
,
Stavber S.
,
Zupan M.
,
Iskra J.
, and
Gladysz J.A.
, J. Org. Chem. , 2009 , 74 , 3133 .
25.
Liu J.
,
Li W.
,
Wang C.
,
Li Y.
, and
Li Z.
, Tetrahedron Lett. , 2011 , 52 , 4320 .
26.
O'Byrne A.
, and
Evans P.
, Tetrahedron , 2008 , 64 , 8067 .
27.
Hultsch C.
,
Blank O.
,
Wester H.-J.
, and
Heinrich M.R.
, Tetrahedron Lett , 2008 , 49 , 1881 .
28.
Kuang C.
,
Yang Q.
,
Senboku H.
, and
Tokuda M.
, Tetrahedron , 2005 , 61 , 4043 .
29.
Kuang C.
,
Senboku H.
, and
Tokuda M.
, Tetrahedron , 2005 , 61 , 637 .
30.
Ranu B.C.
,
Samanta S.
, and
Guchhait S.K.
, J. Org. Chem. , 2001 , 66 , 4102 .