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 2004(12): 2091-2094
DOI: 10.1055/s-2004-832819
DOI: 10.1055/s-2004-832819
LETTER
© Georg Thieme Verlag Stuttgart · New YorkPt(0)-Catalyzed Alkynylation of Aryl Iodides with Lithium Alkynyltriisopropoxy Borates
Further Information
Received
1 July 2004
Publication Date:
21 September 2004 (online)
Publication History
Publication Date:
21 September 2004 (online)

Abstract
An efficient cross coupling reaction of various lithium alkynyltriiospropoxyborates with a wide array of aryl iodides was catalyzed by Pt(PPh3)4-CuI in DMF as a solvent. These cross coupling reactions are general and permit the new sp-sp2 carbon-carbon bond formation.
Key words
alkynylation - lithium alkynylborate - Pt-catalyst - Suzuki-Miyaura coupling
- For Al see:
- 1a
Gelman D.Tsvelikhosky D.Molander GA.Blum J. J. Org. Chem. 2002, 67: 6287 - 1b
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979 - 1c For Si see:
Nishihara Y.Ikegashira K.Hirabayashi K.Ando J.-I.Mori A.Hiyama T. J. Org. Chem. 2000, 65: 1780 - 1d For Sn see:
Stille JK. Pure Appl. Chem. 1985, 57: 1771 - 1e
Tamao K.Yamaguchi S.Shiro M. J. Am. Chem. Soc. 1994, 116: 11715 - 1f
Echavarren AM.Stille JK. J. Am. Chem. Soc. 1987, 109: 5478 - 1g
Kosugi M.Tamura H.Sano H.Migita T. Chem. Lett. 1987, 193 - 1h For Zn see:
King AO.Okukado N.Negishi E. Chem. Commun. 1997, 683 - 1i
Negishi E. Acc. Chem. Res. 1982, 15: 340 - 1j
Negishi E.Qian M.Zeng F.Anastasia L.Babinski D. Org. Lett. 2003, 5: 1597 - 1k
Negishi E.Kotora M.Xu L. J. Org. Chem. 1997, 62: 8957 - 1l
Yoneda N.Matsuoka S.Miyaura N.Fukuhara J.Suzuki A. Bull. Chem. Soc. Jpn. 1990, 63: 2124 - 2a
Sonogoshira K.Thoda Y.Hagihara N. Tetrahedron Lett. 1975, 6: 4467 - 2b
Takahashi K.Kuroyama Y.Sonogoshira K.Hagihara N. Synthesis 1980, 627 - 2c
Pal M.Parasuraman K.Gupta S.Yeleswarapu KR. Synlett 2002, 1976 - 2d
Mori A.Kawashima J.Shimada J.Suguro M.Hirabayashi K.Nishihara Y. Org. Lett. 2000, 2: 2935 - 2e
Siemen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632 - 3a
Lee C.-H.Yamamoto T. Tetrahedron Lett. 2001, 42: 3993 - 3b
Wolf JJ.Siegler F.Matsuchiner R.Wortman R. Angew. Chem. Int. Ed. 2000, 39: 1436 - 3c
Mastumi N.Naka K.Chujo Y. J. Am. Chem. Soc. 1998, 120: 5112 - 4a
Pugh VJ.Hu Q.-S.Zuo X.Lewis FD.Pu L. J. Org. Chem. 2001, 66: 6136 - 4b
Hu Q.-S.Pugh V.Sabat M.Pu L. J. Org. Chem. 1999, 64: 7528 - 5
Wan WB.Haley MM. J. Org. Chem. 2001, 66: 3893 - 6a
Holl DJ.Mio MJ.Prince RB.Hughes TS.Moore JS. Chem. Rev. 2001, 101: 3893 - 6b
Bunz UHF. Chem. Rev. 2000, 100: 1605 - 7a
Cooke JWB.Bright R.Coleman MJ.Jenkins KP. Org. Process Res. Dev. 2001, 5: 383 - 7b
Arterbun JB.Venkateswara K.Perry R.Perry MC. Tetrahedron Lett. 2000, 41: 839 - 7c
Grissom JW.Gunawaradena GV.Klingberg D.Huang D. Tetrahedron 1996, 52: 6453 - 7d
Miller WM.Johnson CR. J. Org. Chem. 1997, 62: 1582 - 8a
Nicolaou KC.Sorensen EJ. Classics in Total Synthesis Wiley-VCH; Weinheim: 1996. p.582-586 - 8b
Brandsma L.Vasilevsky SF.Verkruijsse HD. Application of Transition Metal Catalysts in Organic Synthesis Springer; Berlin: 1998. p.179-225 - 8c
Tour J. Acc. Chem. Res. 2000, 33: 791 - For reviews see:
- 9a
Miyaura N.Suzuki A. Chem. Rev. 1995, 2457 - 9b
Suzuki A. Pure Appl. Chem. 1994, 66: 213 - 9c
Suzuki A. Acc. Chem. Res. 1982, 15: 178 - 9d
Oh-e T.Miyaura N.Suzuki A. Chem. Lett. 1990, 221 - 9e
Watanabe T.Miyaura N.Suzuki A. Synlett 1992, 207 - 9f
Molander GA.Brown HC. J. Org. Chem. 1977, 42: 3106 - 10a
Molander GA.Katona BW.Machrouhi F. J. Org. Chem. 2002, 67: 8416 - 10b
Oh CH.Jung SH. Tetrahedron Lett. 2000, 41: 8513 - 11a
Chen H.Deng M.-H. J. Org. Metal. Chem. 2000, 603: 189 - 11b
Kobayashi Y.Mizojiri R.Ikeda E. J. Org. Chem. 1996, 61: 5391 - 12a
Chong MJ.Shen L.Nicholas JT. J. Am. Chem. Soc. 2000, 122: 1822 - 12b
Battey AR.Thadani AN.Smil DV. Org. Lett. 1999, 1: 1683 - 12c
Brown CD.Chong JM.Shen L. Tetrahedron 1999, 55: 14233 - 13
Kabalka GW.Venkataiah B.Dong G. Tetrahedron Lett. 2004, 45: 729 - 14
Oh CH.Reddy VR. Tetrahedron Lett. 2004, 45: 5221 - 15a
Kondo T.Tsuji Y.Watanabe Y. J. Organomet. Chem. 1988, 345: 397 - 15b
Oh CH.Lim YM.You CH. Tetrahedron Lett. 2002, 43: 4645 - 15c
Bedford RB.Hazelwood SL. Organometallics 2002, 21: 2559 - 16
Kelker AA. Tetrahedron Lett. 1996, 37: 8917 - 17a
Speier JL.Webster JA.Bernes GH. J. Am. Chem. Soc. 1957, 79: 974 - 17b
Wu W.Li C.-J. Chem. Commun. 2003, 1668 - 18a
Pastine SJ.Youn SW.Sames D. Org. Lett. 2003, 5: 1055 - 18b
Pastine SJ.Youn SW.Sames D. Tetrahedron 2003, 59: 8859 - 18c
Liu C.Han X.Wang X.Widenhoefer RA. J. Am. Chem. Soc. 2004, 126: 3700 - 19a
Brunet J.-J.Cadena M.Chu NC.Diallo O.Jacob K.Mothes E. Organometallics 2004, 23: 1264 - 19b
Wang X.Widenhoefer RA. Organometallics 2004, 23: 1649 - 20a
Oh CH.Jung HH.Kim KS. Angew. Chem. Int. Ed. 2003, 42: 805 - 20b
Oh CH.Ahn TW.Reddy VR. Chem. Commun. 2003, 2622 - 20c
Kim N.Kim KS.Gupta AK.Oh CH. Chem. Commun. 2004, 618 - 20d
Oh CH.Ryu JH. Bull. Korean Chem. Soc. 2003, 24: 1563 - 21a
Clarke ML. Polyhedron 2001, 20: 151 - 21b
Mareo C.Fernadez-Rivas C.Cardenas DJ.Echavarren AM. Organometallics 1998, 17: 3661 - 21c
Merwin RK.Schnabel RC.Koola JD.Roddick DM. Organometallics 1992, 11: 2972 - 22a
Brown HC.Cole TE. Organometallics 1983, 2: 1316 - 22b
Brown HC.Bhatt NG.Srebnik M. Tetrahedron Lett. 1988, 29: 2631