Abstract
Carbon–carbon bond formation is important in organic synthesis for the preparation of natural products, organic materials and polymers and so on. An efficient and mild reductive homocoupling of arylmethyl halides is now described. Treatment of various benzylic halides in the presence of zero valent iron nanoparticles (nZVI) and a catalytic amount of CuBr in air and water at room temperature afforded 1,2-diarylethanes in excellent yields.
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References
1.
Shinokubo H.
, and
Oshima K.
, Eur. J. Org. Chem. , 2004 , 2081 .
2.
hLuh T.Y.
,
Leung M.K.
, and
Wong K.T.
, Chem. Rev. , 2000 , 100 , 3187 .
3.
Wurtz A.
, Ann. Chem. Phys. , 1855 , 44 , 275 .
4.
Hassan J.
,
Sevignon M.
,
Gozzi C.
,
Schulz E.
, and
Lemaire M.
, Chem. Rev. , 2002 , 102 , 1359 .
5.
Diederich F.
, and
Stang P.J.
, Metal-catalysed cross-coupling reactions , Wiley VCH : New York , 1998 .
6.
Qian Y.L.
,
Li G.S.
, and
Huang Y.Z.
, J. Organomet. Chem. , 1990 , 381 , 29 .
7.
Sustmann R.
, and
Kopp C.
, J. Organomet. Chem. , 1988 , 347 , 313 .
8.
Okude Y.
,
Hiyama T.
, and
Nozaki H.
, Tetrahedron Lett. , 1977 , 18 , 3829 .
9.
Nishino T.
,
Watanabe T.
,
Okada M.
,
Nishiyama Y.
, and
Sonoda N.
, J. Org. Chem. , 2002 , 67 , 966 .
10.
Ginah F.O.
,
Donovan T.A.
,
Suchan S.D.
,
Pfennig D.R.
, and
Ebert G.W.
, J. Org. Chem. , 1990 , 55 , 584 .
11.
Inaba S.
,
Matsumoto H.
, and
Rieke R.D.
, J. Org. Chem. , 1984 , 49 , 2093 .
12.
Li C.J.
, and
Chan T.H.
, Organometallics , 1991 , 10 , 2548 .
13.
Khurana J.M.
,
Sushma C.
, and
Maikap G.C.
, Org. Biomol. Chem. , 2003 , 1 , 1337 .
14.
Fürstner A.
, Angew. Chem., Int. Ed. Engl. , 1993 , 32 , 164 .
15.
Alonso A.D.
,
Nájera C.
, and
Pacheco M.C.
, Org. Lett. , 2000 , 2 , 1823 .
16.
Li C.J.
, Tetrahedron , 1996 , 52 , 5643 .
17.
Li C.J.
, and
Chan T.H.
, Organic Reactions in Aqueous Media ; Wiley : New York , 1997 .
18.
Breslow R.
, Acc. Chem. Res. , 2004 , 37 , 471 .
19.
Liu J.
, and
Li B.
, Synth. Commun. , 2007 , 37 , 3273 .
20.
Fendler J.H.
, Nanoparticles and nanostructured films. preparation, characterization and applications , Wiley-VCH : Weinheim, Germany , 1998 .
21.
Kogan V.
,
Aizenshtat Z.
,
Popovitz-Biro R.
, and
Neumann R.
, Org. Lett. , 2002 , 4 , 3529 .
22.
Shekarriz M.
,
Taghipoor S.
,
HajiAliAkbari F.
,
Soleymani Jamarani M.
,
Kaveh-Ahangar R.
, and
Eslamian M.
, Int. J. Nanoparticles , 2010 , 3 , 123 .
23.
de Meijere A.
, and
Diederich F.
, Metal-catalysed cross-coupling reactions , Vol. 1 ; 2nd edn, Wiley-VCH : Weinheim , 2004 , Chap. 1, pp. 1 –39 .
24.
Zartman W.H.
, and
Adkinsr H.
, J. Am. Chem. Soc. , 1932 , 54 , 1668 .
25.
Weis C.D.
, Helv. Chim. Acta , 1966 , 49 , 234 .
26.
Hashimoto I.
,
Tsuruta N.
,
Ryang M.
, and
Tsutsumi S.
, J. Org. Chem. , 1970 , 35 , 3748 .
27.
Azoo J.A.
, and
Grimshaw; J.
J. Chem. Soc. C , 1968 , 2403 .
28.
Fuson R.C.
, and
House H.O.
, J. Am. Chem. Soc. , 1953 , 75 , 1325 .
29.
Inaba S.
,
Matsumoto H.
, and
Rieke R.D.
, J. Org. Chem. , 1984 , 49 , 2093 .
30.
Johnston K.M.
, and
Williams G.H.
, J. Chem. Soc. , 1960 , 1168 .
31.
Buu-Hoi Ng. Ph.
, and
Hoan Ng.
, J. Org. Chem. , 1949 , 14 , 1023 .
32.
Lang K.F.
, and
Buffleb H.
, Chem. Ber. , 1958 , 91 , 2866 .
33.
Kim S.H.
, and
Rieke R.D.
, J. Org. Chem. , 2000 , 65 , 2322 .