Abstract
A novel facile method for the traceless solid-phase synthesis of α-iodo ketones using a recyclable resin-bound selenium bromide reagent is reported. Various ketones and β-dicarbonyl compounds can be converted to the corresponding α-iodo-substituted compounds in excellent yields and purities with simple workup procedure and mild conditions.
References
1.
Erian A.W.
,
Sherif S.M.
, and
Gaber H.M.
, Molecules , 2003 , 8 , 793 .
2.
Seevers R.H.
, and
Counsell R.E.
, Chem. Rev. , 1982 , 82 , 575 .
3.
Cardillo G.
, and
Shimisu M.
, J. Org. Chem. , 1977 , 42 , 4268 .
4.
Rubottom G.M.
, and
Mott R.C.
, J. Org. Chem. , 1979 , 44 , 1731 .
5.
Vankar Y.D.
, and
Kumaravel G.
, Tetrahedron Lett. , 1984 , 25 , 233 .
6.
Okamoto T.
,
Kakinami T.
,
Nishimura T.
,
Hermawan I.
, and
Kajigaeshi S.
, Bull. Chem. Soc. Jpn. , 1992 , 65 , 1731 .
7.
Barluenga J.
,
Marco-Arias M.
,
González-Bobes F.
,
Ballesteros A.
, and
González J.M.
, Chem. Commun. , 2004 , 2616 .
8.
Rao M.L.N.
, and
Jadhav D.N.
, Tetrahedron Lett. , 2006 , 47 , 6883 .
9.
Barluenga J.
,
Martinez-Gallo J.M.
,
Najera C.
, and
Yus M.
, Synthesis , 1986 , 678 .
10.
Bekaert A.
,
Barberan O.
,
Gervais M.
, and
Brion J.-D.
, Tetrahedron Lett. , 2000 , 41 , 2903 .
11.
Stavber S.
,
Jereb M.
, and
Zupan M.
, Chem. Commun. , 2002 , 488 .
12.
Goswami P.
,
Ali S.
,
Khan Md. M.
, and
Khan A.T.
, Arkivoc , 2007 , 82 .
13.
Yin G.D.
,
Gao M.
,
She N.F.
,
Hu S.L.
,
Wu A.X.
, and
Pan Y.J.
, Synthesis , 2007 , 3113 .
14.
Le Bras G.
,
Provot O.
,
Bekaert A.
,
Peyrat J.-F.
,
Alami M.
, and
Brion J.-D.
, Synthesis , 2006 , 1537 .
15.
Stavber G.
,
Iskra J.
,
Zupan M.
, and
Stavber S.
, Green. Chem. , 2009 , 11 , 1262 .
16.
Yusubov M.S.
,
Yusubova R.Y.
,
Funk T.V.
,
Chi K.-W.
,
Kirschning A.
, and
Zhdankin V.V.
, Synthesis , 2010 , 3681 .
17.
Meshram H.M.
,
Reddy P.N.
,
Vishnu P.
,
Sadashiv K.
, and
Yadav J.S.
, Tetrahedron Lett. , 2006 , 47 , 991 .
18.
Lee J.C.
,
Park J.Y.
,
Yoon S.Y.
,
Bae Y.H.
, and
Lee S.J.
, Tetrahedron Lett. , 2004 , 45 , 191 .
19.
Moorthy J.N.
,
Senapati K.
, and
Singhal N.
, Tetrahedron Lett. , 2009 , 50 , 2493 .
20.
Nicolaou K.C.
,
Pastor J.
,
Barluenga S.
, and
Winssinger N.
, Chem. Commun. , 1998 , 1947 .
21.
Sheng S.R.
,
Xin Q.
,
Liu X.L.
,
Sun W.K.
,
Guo R.
, and
Huang X.
, Synthesis , 2006 , 2293 .
