Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2011(7): 883-886
DOI: 10.1055/s-0030-1259724
DOI: 10.1055/s-0030-1259724
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Direct Sequential C-O and C-C Formation via Double sp ² C-H Bond Activations to Construct 6H-Benzo[c]chromen-6-ones
Further Information
Received
4 December 2010
Publication Date:
10 March 2011 (online)
Publication History
Publication Date:
10 March 2011 (online)
Abstract
A new method for the direct ortho acyloxylation of sp ² C-H bond with various carboxylic acids was developed. A novel strategy to synthesize 6H-benzo[c]chromen-6-one derivatives was designed via Pd-catalyzed double activations of adjacent sp ² C-H bonds.
Key words
C-H bond activation - ortho acyloxylation - 6H-benzo[c]chromen-6-one
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Tanahashi T.Kuroishi M.Kuwahara A.Nagakura N.Hamada N. Chem. Pharm. Bull. 1997, 45: 1183 -
1b
Weiss U.Yoshihira K.Highet RJ.White RJ.Wei TT. J. Antibiot. 1982, 35: 1194 -
2a
Madan S.Cheng C.-H. J. Org. Chem. 2006, 71: 8312 -
2b
Bringmann G.Menche D.Mühlbacher J.Reichert M.Saito N.Pfeiffer SS.Lipshutz BH. Org. Lett. 2002, 4: 2833 -
2c
Qabaja G.Jones GB. J. Org. Chem. 2000, 65: 7187 - For reviews on this topic, see:
-
3a
Activation
of Unreactive Bonds and Organic Synthesis
Murai S. Springer-Verlag; Berlin/Heidelberg: 1999. -
3b
Shilov AE.Shul’pin GB. Chem. Rev. 1997, 97: 2879 -
3c
Beccalli EM.Broggini G.Martinelli M.Sottocornola S. Chem. Rev. 2007, 107: 5318 ; and the references therein -
3d
Jia C.Piao D.Oyamada J.Lu W.Kitamura T.Fujiwara Y. Science 2000, 287: 1992 -
3e
Godula K.Sames D. Science 2006, 312: 67 -
3f
Stuart DR.Fagnou K. Science 2007, 316: 1172 -
3g
Li B.Tian S.Fang Z.Shi Z. Angew. Chem. Int. Ed. 2008, 47: 1115 -
3h
Yang S.Li B.Wan X.Shi Z. J. Am. Chem. Soc. 2007, 129: 6066 -
3i
Shi Z.Li B.Wan X.Cheng J.Fang Z.Cao B.Qin C.Wang Y. Angew. Chem. Int. Ed. 2007, 46: 5554 -
4a
Thu HY.Yu WY.Che CM. J. Am. Chem. Soc. 2006, 128: 9048 -
4b
Wan X.Ma Z.Li B.Zhang K.Cao S.Zhang S.Shi Z. J. Am. Chem. Soc. 2006, 128: 7416 -
4c
Tsang WCP.Zheng N.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 14560 -
4d
Giri R.Liang J.Lei JG.Li JJ.Wang DH.Chen X.Naggar IC.Guo C.Foxman BM.Yu JQ. Angew. Chem. Int. Ed. 2005, 44: 7420 -
4e
Giri R.Chen X.Yu JQ. Angew. Chem. Int. Ed. 2005, 44: 2112 -
4f
Dangel BD.Johnson JA.Sames D. J. Am. Chem. Soc. 2001, 123: 8149 -
5a
Desai LV.Stowers KJ.Sanford MS. J. Am. Chem. Soc. 2008, 130: 13285 -
5b
Dick AR.Kampf JW.Sanford MS. J. Am. Chem. Soc. 2005, 127: 12790 -
5c
Kalyani D.Deprez NR.Desai LV.Sanford MS. J. Am. Chem. Soc. 2005, 127: 7330 -
5d
Desai LV.Hull KL.Sanford MS. J. Am. Chem. Soc. 2004, 126: 9542 -
5e
Dick AR.Hull KL.Sanford MS. J. Am. Chem. Soc. 2004, 126: 2300 -
5f
Lyons TW.Sanford MS. Chem. Rev. 2010, 110: 1147 -
6a
Chen X.Hao X.-S.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 6790 -
6b
Wang W.Luo F.Zhang S.Cheng J. J. Org. Chem. 2010, 75: 2415 - 7
Stang PJ.Boehshar M.Wingert H.Kitamura T. J. Am. Chem. Soc. 1988, 110: 3272 -
8a
Alberico D.Scott ME.Lautens M. Chem. Rev. 2007, 107: 174 -
8b
Abe H.Nishioka K.Takeda S.Arai M.Takeuchi Y.Harayama T. Tetrahedron 2005, 46: 3197 -
8c
Takeda S.Abe H.Takeuchi Y.Harayama T. Tetrahedron 2007, 63: 396