Copper(I) Iodide Catalyzed Cross-Coupling
Reaction of Terminal Alkynes with 1-Bromoalkynes: A Simple Synthesis
of Unsymmetrical Buta-1,3-diynes

Shihua Wang; Lin Yu; Pinhua Li; Lingguo Meng; Lei Wang

doi:10.1055/s-0030-1259998

PAPER

Copper(I) Iodide Catalyzed Cross-Coupling Reaction of Terminal Alkynes with 1-Bromoalkynes: A Simple Synthesis of Unsymmetrical Buta-1,3-diynes

Shihua Wang^a, Lin Yu^a, Pinhua Li^a, Lingguo Meng^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@chnu.edu.cn ;

Abstract

Alle Artikel dieser Rubrik

Abstract

A simple synthesis of unsymmetrical buta-1,3-diynes by cross-coupling of terminal alkynes with 1-bromoalkynes in the presence of copper(I) iodide and tris(o-tolyl)phosphine was developed that gives good yields under simple and mild reaction conditions. The scope and limitations of the cross-coupling reaction were investigated.

Key words

alkynes - catalysis - cross-coupling - alkadiynes

Volltext

Referenzen

References

<A NAME="RH15711SS-1A">1a</A> Zeni G. Panatieri RB. Lissner E. Menezes PH. Braga AL. Stefani HA. Org. Lett. 2001, 3: 819

<A NAME="RH15711SS-1B">1b</A> Ratnayake AS. Hemscheidt T. Org. Lett. 2002, 4: 4667

<A NAME="RH15711SS-1C">1c</A> Mayer SF. Steinreiber A. Orru RVA. Faber K. J. Org. Chem. 2002, 67: 9115

<A NAME="RH15711SS-1D">1d</A> Yun H. Danishefsky SJ. J. Org. Chem. 2003, 68: 4519

<A NAME="RH15711SS-1E">1e</A> Kraus GA. Bae J. Schuster J. Synthesis 2005, 3502

<A NAME="RH15711SS-1F">1f</A> Yun H. Chou T.-C. Dong H. Tian Y. Li Y.-M. Danishefsky SJ. J. Org. Chem. 2005, 70: 10375

<A NAME="RH15711SS-2">2</A> Stütz A. Petranyi G. J. Med. Chem. 1984, 27: 1539

<A NAME="RH15711SS-3A">3a</A> Lu Y. Yang Y. Sellinger A. Lu M. Huang J. Fan H. Haddad R. Lopez G. Burn AR. Sasaki DY. Shelnutt J. Brinker CJ. Nature (London, U. K.) 2001, 410: 913

<A NAME="RH15711SS-3B">3b</A> Aida T. Tajima K. Angew. Chem. Int. Ed. 2001, 40: 3803

<A NAME="RH15711SS-3C">3c</A> Yang Y. Lu Y. Lu M. Huang J. Haddad R. Xomeritakis G. Liu N. Malanoski AP. Sturmayr D. Fan H. Sasaki DY. Assink RA. Shelnutt JA. van Swol F. Lopez GP. Burns AR. Brinker CJ.
J. Am. Chem. Soc. 2003, 125: 1269

<A NAME="RH15711SS-4">4</A> Acetylene Chemistry: Chemistry, Biology and Material Science Diederich F. Stang PJ. Tykwinski RR. Wiley-VCH; Weinheim: 2005.

<A NAME="RH15711SS-5A">5a</A> Glaser C. Ber. Dtsch. Chem. Ges. 1869, 2: 422

<A NAME="RH15711SS-5B">5b</A> Glaser C. Ann. Chem. Pharm. 1870, 154: 137

<A NAME="RH15711SS-6A">6a</A> Cameron MD. Bennett GE. J. Org. Chem. 1957, 22: 557

<A NAME="RH15711SS-6B">6b</A> Eglinton G. Galbraith AR. J. Chem. Soc. 1959, 889

<A NAME="RH15711SS-6C">6c</A> Hay AS. J. Org. Chem. 1960, 25: 1275

<A NAME="RH15711SS-6D">6d</A> Hay AS. J. Org. Chem. 1962, 27: 3320

<A NAME="RH15711SS-6E">6e</A> Shun ALKS. Tykwinski RR. Angew. Chem. Int. Ed. 2006, 45: 1034

<A NAME="RH15711SS-6F">6f</A> Nishihara E.-I. Anastasia L. Chem. Rev. 2003, 103: 1979

<A NAME="RH15711SS-7A">7a</A> Rossi R. Carpita A. Bigelli CA. Tetrahedron Lett. 1985, 26: 523

<A NAME="RH15711SS-7B">7b</A> Liu QB. Burton DJ. Tetrahedron Lett. 1997, 38: 4371

<A NAME="RH15711SS-7C">7c</A> Lei A. Srivastava M. Zhang X. J. Org. Chem. 2002, 67: 1969

<A NAME="RH15711SS-7D">7d</A> Li JH. Liang Y. Xie YX. J. Org. Chem. 2005, 70: 4393

<A NAME="RH15711SS-7E">7e</A> Fairlamb IJS. Bäuerlein PS. Marrison LR. Dickinson JM. Chem. Commun. 2003, 632

<A NAME="RH15711SS-8A">8a</A> Hébert N. Beck A. Lennox RB. Just G. J. Org. Chem. 1992, 57: 1777

<A NAME="RH15711SS-8B">8b</A> Menger FM. Chen XY. Brocchini S. Hopkins HP. Hamilton D. J. Am. Chem. Soc. 1993, 115: 6600

<A NAME="RH15711SS-8C">8c</A> McCallien DWJ. Sanders JKM. J. Am. Chem. Soc. 1995, 117: 6611

<A NAME="RH15711SS-8D">8d</A> Martin RE. Mäder T. Diederich F. Angew. Chem. Int. Ed. 1999, 38: 817

<A NAME="RH15711SS-8E">8e</A> Höger S. Meckenstock A.-D. Pellen H. J. Org. Chem. 1997, 62: 4556

<A NAME="RH15711SS-8F">8f</A> Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632

<A NAME="RH15711SS-8G">8g</A> Xie X. Phuan P.-W. Kozlowski MC. Angew. Chem. Int. Ed. 2003, 42: 2168

<A NAME="RH15711SS-8H">8h</A> Valenti E. Pericas MA. Serratosa F. J. Am. Chem. Soc. 1990, 112: 7405

<A NAME="RH15711SS-9">9</A> Yin W. He C. Chem M. Zhang H. Lei A. Org. Lett. 2009, 11: 709 ; and references cited therein

<A NAME="RH15711SS-10A">10a</A> Kim S. Kim S. Lee T. Ko H. Kim D. Org. Lett. 2004, 6: 3601

<A NAME="RH15711SS-10B">10b</A> Nishihara Y. Ikegashira K. Mori A. Hiyama T. Tetrahedron Lett. 1988, 39: 4075

<A NAME="RH15711SS-10C">10c</A> Montierth JM. Demario DR. Kurth MJ. Schore NE. Tetrahedron 1998, 54: 11741

<A NAME="RH15711SS-10D">10d</A> Alami M. Ferri F. Tetrahedron Lett. 1996, 37: 2763

<A NAME="RH15711SS-11">11</A> Shi W. Luo Y. Luo X. Chao L. Zhang H. Wang J. Lei A. J. Am. Chem. Soc. 2008, 130: 14713

<A NAME="RH15711SS-12">12</A> Negishi E. Hata M. Xu C. Org. Lett. 2000, 2: 3687

<A NAME="RH15711SS-13">13</A> Ziegler CB. Harris SM. Baldwin JE. J. Org. Chem. 1987, 52: 443

<A NAME="RH15711SS-14">14</A> Liang Y. Tao L.-M. Zhang Y.-H. Li J.-H. Synthesis 2008, 3988

<A NAME="RH15711SS-15">15</A> Damle SV. Seomoon D. Lee PH. J. Org. Chem. 2003, 68: 7085

<A NAME="RH15711SS-16">16</A> Yu M. Pan D. Jia W. Chen W. Jiao N. Tetrahedron Lett. 2010, 51: 1287

Zusatzmaterial

Supporting Information