Abstract
The homocoupling reaction of aryl chlorides was successfully performed in one-pot without preparation of a Grignard reagent in advance. Various aryl chlorides underwent homocoupling reactions affording the corresponding symmetrical biaryls in moderate to good yields. The nickel triflate catalyst was recovered easily and reused smoothly with only a little loss of its activity.
References
1.
Tamao K.
,
Sumitani K.
, and
Kumada M.
, J. Am. Chem. Soc. , 1972 , 94 , 4374 .
2.
Corriu K.J. P.
, and
Masse J. P.
, J. Chem. Soc., Chem. Commun. , 1972 , 144 .
3.
Tsuji J.
, Palladium reagents and catalysts: innovations in organic synthesis , Wiley , New York : 1996 .
4.
Negishi E.
, Ed. Handbook of organopalladium chemistry for organic synthesis , Wiley , New York : 2002 .
5.
Kohei T.
, J. Organomet. Chem. , 2002 , 653 , 23 .
6.
Volker P.W.
,
Bohm T. W.
,
Christin W. K.
,
Stottmayr G.
, and
Wolfgang A. H.
, Angew. Chem. Int. Ed , 2000 , 39 , 1602 .
7.
Lutz A.
,
Robert B.
,
Julia H. S.
, and
Daniel M.
, Angew. Chem. Int. Ed. , 2005 , 44 , 7216 .
8.
Naohiko Y.
,
Hiroko M.
, and
Eiichi N.
, J. Am. Chem. Soc. , 2005 , 127 , 7978 .
9.
Zhao J.W.
,
Song L. P.
,
Wang Y. K.
, and
Zhu S. Z.
J. Fluor. Chem. , 2006 , 127 , 405 .
10.
Joffrey W.
,
Agnes L.
,
Michael N.
,
Daran J. C.
, and
Rinaldo P.
, J. Mol. Catal. A: Chem. , 2006 , 259 , 205 .
11.
Volker P.W.
,
Wolfgang A.
,
Thomas W.
,
Christian W. K.
, and
Herrmann P.
, Angew. Chem. Int. Ed , 2000 , 39 , 1602 .
12.
Joffrey W.
,
Agnes L.
, and
Rinaldo P.
, J. Organomet. Chem. , 2006 , 691 , 433 .
13.
Kobayashi S.
,
Sugiura M.
,
Kitagawa H.
, and
William W. L.
, Chem. Rev. , 2002 , 102 , 2227 .
14.
Zhang C.
,
Cheng T.
, and
Li R.
, Acta Chim. Sinica. , 2002 , 60 , 481 .
15.
Li X.
,
Du X.
, and
Xu Z.
, Chin. J. Org. Chem. , 2006 , 26 , 1111 .
16.
Lin J.
,
Zheng Y.
, and
Li J.
, J. Zhejiang Univ. Technol. , 2007 , 35 , 190 .
17.
Schwindeman J.A.
,
Sutton D. E.
,
Morrison R. C.
, and
Stryker S. S.
, US 5626798, 1997.
18.
Xu X.L.
,
Cheng D. P.
, and
Pei W.
, J. Org. Chem. , 2006 , 71 , 6637 .
19.
Tashro M.
, and
Yamato T.
, J. Org. Chem. , 1979 , 44 , 3037 .
20.
Watanabe M.
, and
Koie Y.
, JP 11158103, 1999 .
21.
Ma N.
,
Zhu Z.
, and
Wu Y.
, Tetrahedron , 2007 , 63 , 4625 .
22.
Chao C.S.
,
Cheng C. H.
, and
Chang T. T.
, J. Org. Chem. , 1983 , 48 , 4909 .
23.
Wang L.
,
Zhang Y.
, and
Liu L.
, J. Org. Chem. , 2006 , 71 , 1284 .