Abstract
A Pd(II)-catalysed homocoupling of sodium arylsulfinates has been successfully achieved under mild conditions. This transformation is a new method for the homocoupling reaction of sodium arylsulfinates, thus providing an alternative synthesis of symmetric biaryls. The reported homocoupling reaction is tolerant to many common functional groups, such as ester, halo, cyano and nitro and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported desulfinative homocoupling does not require Cu salts, ligands and bases, making this newly developed transformation attractive.
References
1.Metal-catalyzed cross-coupling reactions , eds
de Meijere A.
, and
Diederich F.
, 2nd edn. Wiley–VCH , Weinheim, Germany , 2004 .
2.
Jana R.
,
Pathak T.P.
, and
Sigman M.S.
Chem. Rev. , 2011 , 111 , 1417 .
3.Metal-catalyzed cross-coupling reactions and more , eds
de Meijere A.
,
Bräse S.
, and
Oestreich M.
Wiley–VCH , Weinheim, Germany , 2014 .
4.New trends in cross-xoupling theory and applications , ed.
Colacot T.J.
The Royal Society of Chemistry , Cambridge , 2015 .
5.
Ullmann F.
, and
Bielecki J.
, Ber. Dt sch. Chem. Ges. , 1901 , 34 , 2174 .
6.
Hassan J.
,
Sévignon M.
,
Gozzi C.
,
Schulz E.
, and
Lemaire M.
, Chem. Rev. , 2002 , 102 , 1359 .
7.
Rosen B.M.
,
Quasdorf K.W.
,
Wilson D.A.
,
Zhang N.
,
Resmerita A.M.
,
Garg N.K.
, and
Percec V.
, Chem. Rev. , 2011 , 111 , 1346 .
8.
Piers E.
,
Yee J.G.K.
, and
Gladstone P.L.
, Org. Lett. , 2000 , 2 , 481 .
9.
Maji M.S.
,
Pfeifer T.
, and
Studer A.
, Angew. Chem., Int. Ed. , 2008 , 47 , 9547 .
10.
Amatore C.
,
Cammoun C.
, and
Jutand A.
, Eur. J. Org. Chem. , 2008 , 4567 .
11.
Cheng G.J.
, and
Luo M.M.
, Eur. J. Org. Chem. , 2011 , 2519 .
12.
Cornella J.
,
Lahlali H.
, and
Larrosa I.
, Chem. Commun. , 2010 , 46 , 8276 .
13.
Zhao Q.
,
Chen L.
,
Lang H.
,
Wu S.
, and
Wang L.
Chin. J. Chem. , 2015 , 33 , 535 .
14.
Kashiwabara T.
, and
Tanaka M.
, Tetrahedron Lett. , 2005 , 46 , 7125 .
15.
Zhang W.
,
Zhao B.
, and
Li K.
J. Chem. Res. , 2013 , 37 , 674 .
16.
Yu H.-Z.
,
Fu F.
,
Zhang L.
,
Fu Y.
,
Dang Z.-M.
, and
Shi J.
, Phys. Chem. Chem. Phys. , 2014 , 16 , 20964 .
17.
Deng G. J.
,
Zhou X.
,
Luo J.
,
Liu J.
, and
Peng S.
, Org. Lett. , 2011 . 13 , 1432 .
18.
Hu S.
,
Xia P.
,
Cheng K.
, and
Qi C.
, Appl. Organometal. Chem. , 2013 , 27 , 188 .
19.
Cheng K.
,
Hu S.
,
Zhao B.
,
Zhang X.-M.
, and
Qi C.
, J. Org. Chem. , 2013 , 78 , 5022 .
20.
20
Cheng K.
,
Yu H.-Z.
,
Zhao B.
,
Hu S.
,
Zhang X.-M.
, and
Qi C.
, RSC Adv. , 2014 , 4 , 57923 .
21.
You J.
,
Liu B.
,
Guo Q.
,
Cheng Y.
, and
Lan J.
, Chem.-Eur. J. , 2011 , 17 , 13415 .
22.
Deng G.J.
,
Chen R.
,
Liu S.
,
Liu X.
, and
Luo Y.
, Org. Biomol. Chem. , 2011 , 9 , 7675 .
23.
Wang L.
,
Wang M.
,
Li D.
, and
Zhou W.
, Tetrahedron , 2012 , 68 , 1926 .
24.
Deng G.J.
,
Luo H.A.
,
Wu M.
,
Luo J.
,
Xiao F.
, and
Zhang S.
, Adv. Synth. Catal. , 2012 , 354 , 335 .
25.
Li C.J.
,
Rao H.
,
Yang L.
, and
Shuai Q.
, Adv. Synth. Catal. , 2011 , 353 , 1701 .
26.
Liu S.
,
Bai Y.
,
Cao X.
,
Xiao F.
, and
Deng G. J.
, Chem. Commun. , 2013 , 49 , 7501 .
27.
Xu Y.
,
Zhao J.
,
Tang X.
,
Wu W.
, and
Jiang H.
, Adv. Synth. Catal. , 2014 , 356 , 2029 .
28.
Deng G.J.
,
Li C.J.
,
Liu J.
,
Zhou X.
,
Rao H.
, and
Xiao F.
, Chem.-Eur. J. , 2011 , 17 , 7996 .
29.
Kantam M.L.
,
Neelima B.
,
Sreedhar B.
, and
Chakravarti R.
, Synlett , 2008 , 1455 .
30.
Forgione P.
,
Ortgies D.H.
,
Barthelme A.
,
Aly S.
,
Desharnais B.
, and
Rioux S.
, Synthesis , 2013 , 45 , 694
31.
Liu B.
,
Guo Q.
,
Cheng Y.
,
Lan J.
, and
You J.
, Chem.-Eur. J. , 2011 , 17 , 13415 .
32.
Rao B.
,
Zhang W.X.
,
Hu L.
, and
Luo M.M.
, Green Chem. , 2012 , 14 , 3436 .
33.
Ortgies D.H.
,
Chen F.
, and
Forgione P.
, Eur. J. Org. Chem. , 2014 , 3917 .
34.
Zhang W.
,
Liu F.
,
Li K.
, and
Zhao B.
Appl. Organometal. Chem. , 2014 , 28 , 379 .
35.
Zhang W.
,
Li K.
, and
Zhao B.
, J. Chem. Res. , 2014 , 38 , 269 .
36.
Zhang W.
,
Liu F.
, and
Zhao B.
Appl. Organometal. Chem. , 2015 , 29 , 524 .
37.
Peng Y.
J. Chem. Res. , 2014 , 38 , 265 .
38.
Kirai N.
, and
Yamamoto Y.
, Eur. J. Org. Chem. , 2009 , 1864 .
39.
Cahiez G.
,
Moyeux A.
,
Buendia J.
, and
Duplais C.
, J. Am. Chem. Soc. , 2007 , 129 , 13788 .
40.
Yuan Y.
, and
Bian Y.
, Appl. Organomet. Chem. , 2008 , 22 , 15 .
41.
Cahiez G.
,
Chaboche C.
,
Mahuteau Betzer F.
,
Ahr M.
, Org. Lett. , 2005 , 7 , 1943 .
42.
Kumar M.R.
,
Park K.
, and
Lee S.
, Adv. Synth. Catal. , 2010 , 352 , 3255 .
43.Organic solvents: physical properties and methods of purification , eds
Riddick J.A.
,
Bunger W.B.
, and
Sakano T.K.
, 4th edn. Wiley–VCH , Weinheim, Ger many , 1986 .
44.
Yang F.-L.
,
Ma R.-T.
, and
Tian S.-K.
, Chem. Eur.-J. , 2012 , 18 , 1582 .