RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2003(15): 2390-2394
DOI: 10.1055/s-2003-42438
DOI: 10.1055/s-2003-42438
PAPER
© Georg Thieme Verlag Stuttgart · New York
InBr3-Catalyzed Alkynylation and Allylation of Acid Chlorides: A Facile Synthesis of Alkynyl and Allyl Ketones
Weitere Informationen
Received
2 June 2003
Publikationsdatum:
23. Oktober 2003 (online)
Publikationsverlauf
Publikationsdatum:
23. Oktober 2003 (online)
![](https://www.thieme-connect.de/media/synthesis/200315/lookinside/thumbnails/10.1055-s-2003-42438-1.jpg)
Abstract
Alkynylsilanes and allyltrimethylsilane undergo smooth coupling with acid chlorides in the presence of 5 mol% of indium tribromide under mild conditions to afford the corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in excellent yields in a short reaction time with high selectivity.
Key words
indium reagents - acid chlorides - α,β- and β,γ-unsaturated ketones
-
1a
Thompson CF.Jamison TF.Jacobsen EN. J. Am. Chem. Soc. 2001, 123: 9974 -
1b
Li P.Fong WM.Chao LCF.Fung SHC.Williams ID. J. Org. Chem. 2001, 66: 4087 -
1c
Adlington RM.Baldwin JE.Pritchard GJ.Spencer KC. Tetrahedron Lett. 2000, 41: 575 -
1d
Kel’in AV.Gevorgyan V. J. Org. Chem. 2002, 67: 95 -
1e
Bagley MC.Dale JW.Bower J. Chem. Commun. 2002, 1682 -
2a
Perollier C.Sorokin AB. Chem. Commun. 2002, 1548 -
2b
Basak A.Bdour HM.Shain JC.Mandal S.Rudra KR.Nag S. Bioorg. Med. Chem. Lett. 2000, 10: 1321 -
2c
Baldwin JE.Pritchard GJ.Rathmell RE. J. Chem. Soc., Perkin Trans. 1 2001, 2906 -
3a
Davis RB.Scheiber DH. J. Am. Chem. Soc. 1956, 78: 1675 -
3b
Normant JF. Synthesis 1972, 63 -
3c
Yamaguchi M.Shibato K.Fujuwara S.Hirao I. Synthesis 1986, 421 -
3d
Chowdhury C.Kundu N. Tetrahedron 1999, 55: 7011 -
4a
Walton DRM.Waugh F. J. Organomet. Chem. 1972, 37: 45 -
4b
Ito H.Arimoto K.Sensui H.Hosomi A. Tetrahedron Lett. 1997, 38: 3977 -
4c
Logue MW.Teng K. J. Org. Chem. 1982, 47: 2549 -
4d
Shun ALKS.Chernick ET.Eisler S.Tykwinski RR. J. Org. Chem. 2003, 68: 1339 - 5
Maeda Y.Kakiuchi N.Matsumura S.Nishimura T.Kawamura T.Uemura S. J. Org. Chem. 2002, 67: 6718 ; and references cited therein -
6a
Schimdt U.Schwochau M. Chem. Ber. 1964, 97: 1649 -
6b
Tohda Y.Sonogashira K.Hagihara N. Synthesis 1977, 777 -
6c
Birkofer L.Ritter A.Uhlenbrauck H. Chem. Ber. 1963, 96: 3280 -
7a
Li CJ.Chan TH. Tetrahedron 1999, 55: 11149 -
7b
Babu G.Perumal PT. Aldrichimica Acta 2000, 33: 16 -
7c
Ghosh R. Indian J. Chem., Sect. B 2001, 40: 550 -
8a
Ceschi MA.Felix LA.Peppe C. Tetrahedron Lett. 2000, 41: 9695 -
8b
Bandini M.Cozzi GP.Giocomini M.Melchiorre P.Selva S.Umani-Ronchi A. J. Org. Chem. 2002, 67: 3700 -
9a
Yadav JS.Reddy BVS. Synthesis 2002, 511 -
9b
Yadav JS.Reddy BVS.Raju AK.Rao CV. Tetrahedron Lett. 2002, 43: 5437