Abstract
A novel method for the stereoselective synthesis of (Z)-β-arylvinyl bromides in excellent yields by debrominative decarboxylation of anti-2,3-dibromo-3-arylpropanoic acids using NaN3 was developed. This facile transformation was achieved under room temperature for 1–2 h.
References
1.
Espinet P.
, and
Echavarren A.M.
, Angew. Chem. Int. Ed. , 2004 , 43 , 4704 .
2.
Miyaura N.
, and
Suzuki A.
, Chem. Rev. , 1995 , 95 , 2457 .
3.
Li J.H.
,
Li J.L.
,
Wang D.P.
,
Pi S.F.
,
Xie Y.X.
,
Zhang M.B.
, and
Hu X.C.
, J. Org. Chem. , 2007 , 72 , 2053 .
4.
Liao Q.
,
Wang Y.X.
,
Zhang L.Y.
, and
Xi C.J.
, J. Org. Chem. , 2009 , 74 , 6371 .
5.
Negishi E.
, and
Anastasia L.
, Chem. Rev. , 2003 , 103 , 1979 .
6.
Saha D.
,
Chatterjee T.
,
Mukherjee M.
, and
Ranu B.C.
, J. Org. Chem. , 2012 , 77 , 9379 .
7.
Jiang L.
,
Job G.E.
,
Klapars A.
, and
Buchwald S.L.
, Org. Lett. , 2003 , 5 , 3667 .
8.
Smithers R.H.
, J. Org. Chem. , 1978 , 43 , 2833 .
9.
Matsumoto M.
, and
Kuroda K.
, Tetrahedron Lett. , 1980 , 21 , 4021 .
10.
Stork G.
, and
Zhao K.
, Tetrahedron Lett. , 1989 , 30 , 2173 .
11.
Zhang X.P.
, and
Schlosser M.
, Tetrahedron Lett. , 1993 , 34 , 1925 .
12.
Morrill C.
, and
Grubbs R.H.
, J. Org. Chem. , 2003 , 65 , 6031 .
13.
Petasis N.A.
, and
Zavialov I.A.
, Tetrahedron Lett. , 1996 , 37 , 567 .
14.
Miller R.B.
, and
McGarvey G.
, J. Org. Chem. , 1978 , 43 , 4424 .
15.
Brown H.C.
,
Blue C.D.
,
Nelson D.J.
, and
Bhat N.G.
, J. Org. Chem. , 1989 , 54 , 6064 .
16.
Brown H.C.
,
Subrahmanyam C.
,
Hanaoka T.
,
Ravindran N.
,
Bowman D.H.
,
Misumi S.
,
Unni M.K.
,
Somayaji V.
, and
Bhat N.G.
, J. Org. Chem. , 1989 , 54 , 6068 .
17.
Uenishi J.
,
Kawahama R.
,
Shiga Y.
, and
Yonemitsu O.
, Tetrahedron Lett. , 1996 , 37 , 6759 .
18.
Uenishi J.
,
Kawahama R.
,
Yonemitsu O.
, and
Tsuji J.
, J. Org. Chem. , 1998 , 63 , 8965 .
19.
Lebrun M.E.
,
Marquand P.L.
, and
Berthelette C.
, J. Org. Chem. , 2006 , 71 , 2009 .
20.
Grovenstein J.E.
, and
Lee D.E.
, J. Am. Chem. Soc. , 1953 , 75 , 2639 .
21.
Cristol S.J.
, and
Norris W.P.
, J. Am. Chem. Soc. , 1953 , 75 , 2645 .
22.
Paquette L.A.
,
Fristad W.E.
,
Dime D.S.
, and
Bailey T.R.
, J. Org. Chem. , 1980 , 45 , 3017 .
23.
Matveeva E.D.
,
Erin A.S.
, and
Kurz A.L.
, Russ. J. Org. Chem. , 1997 , 33 , 1065 .
24.
Kim S.H.
,
Wei H.X.
,
Willis S.
, and
Li G.
, Synth. Commun. , 1999 , 29 , 4179 .
25.
Kuang C.X.
,
Senboku H.
, and
Tokuda M.
, Tetrahedron Lett. , 2001 , 42 , 3893 .
26.
Kuang C.X.
,
Yang Q.
,
Senboku H.
, and
Tokuda M.
, Tetrahedron , 2005 , 61 , 4043 .
27.
Jiang Y.B.
, and
Kuang C.X.
, Synth. Commun. , 2009 , 39 , 4298 .
28.
Zhang W.S.
,
Kuang C.X.
, and
Yang Q.
, Z. Naturforsch. , 2009 , 64b , 292 .
29.
Ranu B.C.
,
Banerjee S.
, and
Gupta J.
, Synth. Commun. , 2007 , 37 , 2869 .
30.
Zhang W.S.
,
Kuang C.X.
, and
Yang Q.
, Synthesis , 2010 , 283 .
