Abstract
α or β-hydroxy propargylic alcohols undergo tandem C(sp)–C(sp3) bond cleavage via β-alkynyl elimination and homo-coupling of the resulted alkynyl species in the presence of Cu(OAc)2·H2O to produce the corresponding hydroxycarbonyl compounds and 1,3-butadiynes.
References
1.
Shintani R.
,
Takatsu K.
,
Katoh T.
,
Nishimura T.
, and
Hayashi T.
, Angew. Chem. Int. Ed. , 2008 , 47 , 1447 .
2.
Horita A.
,
Tsurugi H.
,
Funayama A.
,
Satoh T.
, and
Miura M.
, Org. Lett. , 2007 , 9 , 2231 .
3.
Nishimura T.
,
Araki H.
,
Maeda Y.
, and
Uemura S.
, Org. Lett. , 2003 , 5 , 2997 .
4.
Nishimura T.
,
Katoh T.
,
Takatsu K.
,
Shintani R.
, and
Hayashi T.
, J. Am. Chem. Soc. , 2007 , 129 , 14158 .
5.
Funayama A.
,
Satoh T.
, and
Miura M.
, J. Am. Chem. Soc. , 2005 , 127 , 15354
6.
Sugiishi T.
,
Kimura A.
, and
Nakamura H.
, J. Am. Chem. Soc. , 2010 , 132 , 5332
7.
Susanti D.
,
Koh F.
,
Kusuma J.A.
,
Kothandaraman P.
, and
Chan P.W.H.
, J. Org. Chem. , 2012 , 77 , 7166 .
8.
Harkat H.
,
Blanc A.L.
,
Weibel J.-M.
, and
Pale P.
, J. Org. Chem. , 2008 , 73 , 1620 .
9.
Kumar G.S.
,
Maheswari C.U.
,
Kumar R.A.
,
Kantam M.L.
, and
Reddy K.R.
, Angew. Chem. Int. Ed. , 2011 , 50 , 11748 .
10.
Egglinton G.
, and
McRae W.
, Adv. Org. Chem. , 1963 , 4 , 225 .
11.
Harkat H.
,
Blanc A.L.
,
Weibel J.-M.
, and
Pale P.
, J. Org. Chem. , 2008 , 73 , 1620 .
12.
Antczak M.I.
,
Cai F.
, and
Ready J.M.
, Org. Lett. , 2011 , 13 , 184 .
13.
Adimurthy S.
,
Malakar C.C.
, and
Beifuss U.
, J. Org. Chem. , 2009 , 74 , 5648 .
14.
Meng X.
,
Li C.B.
,
Han B.C.
,
Wang T.S.
, and
Chen B.H.
, Tetrahedron. , 2010 , 66 , 4029 .
15.
Eugen M.
,
Dominik U.
, and
Thomas M.J.J.
, Eur. J. Org. Chem. , 2011 , 238 .
16.
Wu T.M.
,
Huang S.H.
, and
Tsai F.Y.
, Appl. Organomet. Chem. , 2011 , 25 , 395 .
17.
Kumar V.
,
Chipeleme A.
, and
Chibale K.
, Eur. J. Org. Chem. , 2008 , 43 .
18.
Yin K.
,
Li C.J.
,
Li J.
, and
Jia X.S.
, Green Chem. , 2011 , 13 , 591 .