Abstract
The efficient conversion of boronic acids, both arylboronic acids and alkylboronic acids, to the corresponding amines in water was accomplished in moderate to good yields using Cu(NO3)2 complexes of amines as the nitrogen source. The coupling reactions were performed in water at 30 °C for 2 hours.
Keywords
References
1.
Louie J.
, and
Hartwig J.F.
, J. Am. Chem. Soc. , 1997 , 119 , 11695 .
2.
Singer R.A.
,
Sadighi J.P.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 1998 , 120 , 213 .
3.
Shen Q.
, and
Hartwig J.F.
, J. Am. Chem. Soc. , 2006 , 128 , 10028 .
4.
Xia N.
, and
Taillefer M.
, Angew. Chem. Int. Ed. , 2009 , 48 , 337 .
5.
Xu H.
, and
Wolf C.
, Chem. Commun. , 2009 , 3035 .
6.
Fors B.P.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2009 , 131 , 12898 .
7.
Rao H.
,
Fu H.
,
Jiang Y.
, and
Zhao Y.
, Angew. Chem. Int. Ed. , 2009 , 48 , 1114 .
8.
Prakash G.K.S.
,
Panja C.
,
Mathew T.
,
Surampudi V.
,
Petasis N.A.
, and
Olah G.A.
, Org. Lett. , 2004 , 6 , 2205 .
9.
Prakash G.K.S.
, and
Mathew T.
, Angew. Chem. Int. Ed. , 2010 , 49 , 1726 .
10.
Chan D.M.T.
,
Monaco K.L.
,
Wang R.P.
, and
Winters M.P.
, Tetrahedron Lett. , 1998 , 39 , 2933 .
11.
Evans D.A.
,
Katz J.L.
, and
West T.R.
, Tetrahedron Lett. , 1998 , 39 , 2937 .
12.
Lam P.Y.S.
,
Clark C.G.
,
Saubern S.
,
Adams J.
,
Winters M.P.
,
Chan D.M.T.
, and
Combs A.
, Tetrahedron Lett. , 1998 , 39 , 2941 .
13.
Combs A.P.
,
Saubern S.
,
Rafalski M.
, and
Lam P.Y.S.
, Tetrahedron Lett. , 1999 , 40 , 1623 .
14.
Antilla J.C.
, and
Buchwald S.L.
, Org. Lett. , 2001 , 3 , 2077 .
15.
Lam P.Y.S.
,
Vincent G.
,
Bonne D.
, and
Clark C.G.
, Tetrahedron Lett. , 2003 , 44 , 4927 .
16.
Zhou C.F.
,
Yang D.P.
,
Jia X.F.
, and
Zhang L.X.
, Synlett , 2009 , 19 , 3198 .
17.
Rankovic Z.
,
Cai J.Q.
,
Fradera X.
,
Dempster M.
,
Mistry A.
,
Mitchell A.
,
Long C.
,
Hamilton E.
,
King A.
,
Boucharens S.
,
Jamieson C.
,
Gillespie J.
,
Cumming I.
,
Uitdehaag J.
, and
van Zeeland M.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 1488 .
18.
Park C.H.
,
Chun K.
,
Joe B.Y.
,
Park J.S.
,
Kim Y.C.
,
Choi J.S.
,
Ryu D.K.
,
Koh S.H.
,
Cho G.W.
,
Kim S.H.
, and
Kim M.H.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 2250 .
19.
Liu Y.
,
Xia Y.
,
Fan Y.T.
,
Maggiani A.
,
Rocchi P.
,
Qu F.
,
Iovanna J.L.
, and
Peng L.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 2503 .
20.
Collman J.P.
,
Zhong M.
,
Zhang C.
, and
Costanzo S.
, J. Org. Chem. , 2001 , 66 , 7892 .
21.
Combs A.P.
,
Tadesse S.
,
Rafalski M.
,
Haque T.S.
, and
Lam P.Y.S.
, J. Comb. Chem. , 2002 , 4 , 179 .
22.
Yu S.
,
Saenz J.
, and
Srirangam J.K.
, J. Org. Chem. , 2002 , 67 , 1699 .
23.
Kabalka G.W.
, and
Guchhait S.K.
, Org. Lett. , 2003 , 5 , 4129 .
24.
Uemura T.
, and
Chatani N.
, J. Org. Chem. , 2005 , 70 , 8631 .
25.
Reddy K.R.
,
Kumar N.S.
,
Sreedhar B.
, and
Kantam M.L.
, J. Mol. Catal. A: Chem. , 2006 , 252 , 136 .
26.
Dai Q.
,
Ran C.Z.
, and
Harvey R.G.
, Tetrahedron , 2006 , 62 , 1764 .
27.
Liu S.B.
,
Yu Y.
, and
Liebeskind L.S.
, Org. Lett. , 2007 , 9 , 1947 .
28.
Fang Y.Q.
, and
Lautens M.
, J. Org. Chem. , 2008 , 73 , 538 .
29.
Li Y.
,
Gao L.X.
, and
Han F.S.
, Chem. Eur. J. , 2010 , 16 , 7969 .
30.
Darensbourg D.J.
,
Longridge E.M.
,
Khandelwal B.
, and
Reibenspies J.H.
, J. Coord. Chem. , 1994 , 32 , 27 .
31.
Mel¢nikova N.B.
,
Ioffe I.D.
, and
Tsareva L.A.
, Chem. Nat. Compd. , 2002 , 38 , 33 .
32.
Jia X.
,
Zhu W.
,
Zhang Y.
, and
Yan X.
, J. Mol. Struct. , 2002 , 604 , 159 .
33.
Paine A.J.
, J. Am. Chem. Soc. , 1987 , 109 , 1496 .
34.
Lukes R.
, and
Ferles M.
, Chem. Listy , 1956 , 50 , 1471 .
35.
Hickinbottom W.J.
, J. Chem. Soc. , 1930 , 992 .
36.
Gribble G.W.
, and
Nutaitis C.F.
, Synthesis , 1987 , 8 , 709 .
37.
Zhang Z.
,
Mao J.
,
Zhu D.
,
Wu F.
,
Chen H.
, and
Wan B.
, Tetrahedron , 2006 , 62 , 4435 .
38.
Scott F.L.
,
Ahearne A.
, and
Reilly J.
, J. Org. Chem. , 1957 , 22 , 1688 .
39.
Organ M.G.
,
Abdel-Hadi M.
,
Avola S.
,
Dubovyk I.
,
Hadei N.
,
Kantchev E.A.B.
,
O'Brien C.J.
,
Sayah M.
, and
Valente C.
, Chemistry—Eur. J. , 2008 , 14 , 2443 .
40.
Anderson K.W.
,
Mendez-Perez M.
,
Priego J.
, and
Buchwald S. L.
, J. Org. Chem. , 2003 , 68 , 9563 .
41.
Cretcher L.H.
, and
Pittenger W. H.
, J. Am. Chem. Soc. , 1925 , 47 , 163 .
42.
Stroh H.H.
, Chem. Ber. , 1958 , 91 , 2645 .
43.
Cawley M.J.
,
Cloke F.G.N.
,
Fitzmaurice R. J.
,
Pearson S.E.
,
Scott J.S.
, and
Caddick S.
, Org. Biomol. Chem. , 2008 , 6 , 2820 .
44.
Fors B.P.
, and
Buchwald S. L.
, J. Am. Chem. Soc. , 2010 , 132 , 15914 .
45.
Braun J.
, and
Braunsdorf O.
, Ber. Chem. , 1921 , 54 , 2081 .
