Addition of Terminal Alkynes to Aromatic Nitriles Catalyzed by Divalent 
Lanthanide Amides Supported by Amidates: Synthesis of Ynones

Hao Ding; Chengrong Lu; Xiaolin Hu; Bei Zhao; Bing Wu; Yingming Yao

doi:10.1055/s-0033-1338446

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(10): 1269-1274
DOI: 10.1055/s-0033-1338446

letter

Addition of Terminal Alkynes to Aromatic Nitriles Catalyzed by Divalent Lanthanide Amides Supported by Amidates: Synthesis of Ynones

Hao Ding

College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880305 eMail: zhaobei@suda.edu.cn

,

Chengrong Lu

College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880305 eMail: zhaobei@suda.edu.cn

,

Xiaolin Hu

College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880305 eMail: zhaobei@suda.edu.cn

,

Bei Zhao*

College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880305 eMail: zhaobei@suda.edu.cn

,

Bing Wu

College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880305 eMail: zhaobei@suda.edu.cn

,

Yingming Yao*

College of Chemistry, Chemical Engineering and Materials Science, Dushu Lake Campus, Soochow University, Suzhou 215123, P. R. of China Fax: +86(512)65880305 eMail: zhaobei@suda.edu.cn

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Abstract

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Abstract

An efficient protocol has been established for the synthesis of conjugated ynones via addition of terminal alkynes to aromatic nitriles, which is catalyzed by novel divalent lanthanide amide complexes. All the reactions gave the products in good to excellent yields at room temperature under solvent-free conditions without any additives. The novel lanthanide amide catalysts were also synthesized and structurally characterized for the first time.

Key words

terminal alkyne - aromatic nitrile - divalent lanthanide complex - amidate - ynone

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Referenzen

References

1a Moteki SA, Han JW, Arimitsu S, Akakura M, Nakayama K, Maruoka K. Angew. Chem. Int. Ed. 2012; 51: 1187
1b Ramachary DB, Venkaiah C, Krishna PM. Chem. Commun. 2012; 48: 2252
1c Shi S.-L, Kanai M, Shibasaki M. Angew. Chem. Int. Ed. 2012; 51: 3932
1d Yamamoto A, Ueda A, Brémond P, Tiseni PS, Kishi Y. J. Am. Chem. Soc. 2012; 134: 893
1e Jiang HF, Pan XY, Huang LB, Zhao J, Shi DB. Chem. Commun. 2012; 48: 4698

2a Sawada Y, Furumi S, Takai A, Takeuchi M, Noguchi K, Tanaka K. J. Am. Chem. Soc. 2012; 134: 4080
2b McLeod MC, Wilson ZE, Brimble MA. J. Org. Chem. 2012; 77: 400
2c Plażuk D, Zakrzewski J, Nakatani K, Makal A, Woźniak K, Domagała S. RSC Adv. 2012; 2: 3512
2d Tsvetkov NP, Bayir A, Schneider S, Brewer M. Org. Lett. 2012; 14: 264

3a Wu X.-F, Neumann H, Beller M. Chem. Eur. J. 2010; 16: 12104
3b Wu X.-F, Neumann H, Beller M. Angew. Chem. Int. Ed. 2011; 50: 11142
3c Wu X.-F, Sundararaju B, Neumann H, Dixneuf PH, Beller M. Chem. Eur. J. 2011; 17: 106

4a Delude L, Masdeu AM, Alper H. Synthesis 1994; 1149
4b Ahmed MS. M, Mori A. Org. Lett. 2003; 5: 3057
4c Rahman MT, Fukuyama T, Kamata N, Sato M, Ryu I. Chem. Commun. 2006; 2236
4d Liu JM, Peng XG, Sun W, Zhao YW, Xia CG. Org. Lett. 2008; 10: 3933
4e Wang Y, Liu JH, Xia CG. Tetrahedron Lett. 2011; 52: 1587

5 Park A, Park K, Kim Y, Lee S. Org. Lett. 2011; 13: 944

6a Chen L, Li C.-J. Org. Lett. 2004; 6: 3151
6b Alonso DA, Nájera C, Pacheco MC. J. Org. Chem. 2004; 69: 1615
6c Cox RJ, Ritson DJ, Dane TA, Berge J, Charmant JP. H, Kantacha A. Chem. Commun. 2005; 1037
6d Baxendale IR, Schou SC, Sedelmeier J, Ley SV. Chem. Eur. J. 2010; 16: 89
6e Santra S, Dhara K, Ranjan P, Bera P, Dash J, Mandal SK. Green Chem. 2011; 13: 3238
6f Bakherad M, Keivanloo A, Bahramian B, Jajarmi S. Synlett 2011; 311

7 Gandeepan P, Parthasarathy K, Su T.-H, Cheng C.-H. Adv. Synth. Catal. 2012; 354: 457
8 Shen QS, Huang W, Wang JL, Zhou XG. Organometallics 2008; 27: 301
9 Stanlake LJ. E, Schafer LL. Organometallics 2009; 28: 3990
10 Thomson JA, Schafer LL. Dalton Trans. 2012; 41: 7897

11a Stanlake LJ. E, Beard JD, Schafer LL. Inorg. Chem. 2008; 47: 8062
11b Wang QW, Zhang FR, Song HB, Zi GF. J. Organomet. Chem. 2011; 696: 2186
11c Zhang FR, Zhang JX, Song HB, Zi GF. Inorg. Chem. Commun. 2011; 14: 72

12a Panda TK, Zulys A, Gamer MT, Roesky PW. J. Organomet. Chem. 2005; 690: 5078
12b Takaki K, Komeyama K, Kobayashi D, Kawabata T, Takehira K. J. Alloys Compd. 2006; 408–412: 432
12c Delbridge EE, Dugah DT, Nelson CR, Skelton BW, White AH. Dalton Trans. 2007; 143
12d Zhou H, Guo HD, Yao YM, Zhou LY, Sun HM, Sheng HT, Zhang Y, Shen Q. Inorg. Chem. 2007; 46: 958
12e Datta S, Gamer MT, Roesky PW. Organometallics 2008; 27: 1207
12f Du Z, Li WB, Zhu XH, Xu F, Shen Q. J. Org. Chem. 2008; 73: 8966
12g Dugah DT, Skelton BW, Delbridge EE. Dalton Trans. 2009; 1436
12h Yang S, Du Z, Zhang Y, Shen Q. Chem. Commun. 2012; 48: 9780
12i Garcia J, Allen MJ. Eur. J. Inorg. Chem. 2012; 4550

13a Frantz DE, Fässler R, Tomooka CS, Carreira EM. Acc. Chem. Res. 2000; 33: 373
13b Nishiura M, Hou Z, Wakatsuki Y, Yamaki T, Miyamoto T. J. Am. Chem. Soc. 2003; 125: 1184
13c Wei C, Mague JT, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5749
13d Nishiura M, Hou Z. J. Mol. Catal. A: Chem. 2004; 213: 101
13e Zhang W.-X, Nishiura M, Hou Z. J. Am. Chem. Soc. 2005; 127: 16788
13f Zhang W.-X, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2008; 47: 9700
13g Wang Z, Wang Y, Zhang W.-X, Hou Z, Xi Z. J. Am. Chem. Soc. 2009; 131: 15108
13h Wang Y, Zhang W.-X, Wang Z, Xi Z. Angew. Chem. Int. Ed. 2011; 50: 8122

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