Synthesis 2014; 46(16): 2168-2174
DOI: 10.1055/s-0033-1341271
special topic
© Georg Thieme Verlag Stuttgart · New York

Direct Gold-Catalyzed Regioselective Tetrafunctionalization of Nonactivated Alkynes

Fang Wei
a   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Email: Xuzh@sdu.edu.cn
,
Xianghua Wang
a   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Email: Xuzh@sdu.edu.cn
,
Shasha Peng
a   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Email: Xuzh@sdu.edu.cn
,
Qiuhui Jia
a   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Email: Xuzh@sdu.edu.cn
,
Chao Jiang
a   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Email: Xuzh@sdu.edu.cn
,
Shili Liu
b   School of Medicine, Shandong University, Jinan 250012, P. R. of China
,
Zhenghu Xu*
a   Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Email: Xuzh@sdu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 27 February 2014

Accepted after revision: 13 April 2014

Publication Date:
12 May 2014 (online)


Abstract

A simple and efficient method based on gold catalysis is reported for the synthesis of halogen-functionalized pyrrolidine ­aminals. A new alkyne tetrafunctionalization strategy is proposed for the first time.

Supporting Information

 
  • References

    • 1a Bataille CJ. R, Donohoe TJ. Chem. Soc. Rev. 2011; 40: 114
    • 1b Chemler SR, Bovino MT. ACS Catal. 2013; 3: 1076
    • 1c Kang Y.-B, Gade LH. J. Am. Chem. Soc. 2011; 133: 3658
    • 1d Wang F, Qi X, Liang Z, Chen P, Liu G. Angew. Chem. Int. Ed. 2014; 53: 1881
    • 2a Yin Q, You S.-L. Org. Lett. 2013; 15: 4266
    • 2b Yin Q, You S.-L. Org. Lett. 2012; 14: 3526
    • 2c Xie W, Jiang G, Liu H, Hu J, Pan X, Zhang H, Wan X, Lai Y, Ma D. Angew. Chem. Int. Ed. 2013; 52: 12924
    • 2d Wu T, Yin G, Liu G. J. Am. Chem. Soc. 2009; 131: 16354
    • 2e Thakur VV, Kumar Talluri S, Sudalai A. Org. Lett. 2003; 5: 861
    • 3a Xue Q, Xie J, Xu P, Hu K, Cheng Y, Zhu C. ACS Catal. 2013; 3: 1365
    • 3b Wang A, Jiang H, Chen H. J. Am. Chem. Soc. 2009; 131: 3846
    • 3c Li Y, Song D, Dong VM. J. Am. Chem. Soc. 2008; 130: 2962
    • 3d Zhang Y, Sigman MS. J. Am. Chem. Soc. 2007; 129: 3076
    • 4a Zhu H, Chen P, Liu G. J. Am. Chem. Soc. 2014; 136: 1766
    • 4b de Haro T, Nevado C. Angew. Chem. Int. Ed. 2011; 50: 906
    • 4c Michaelis DJ, Shaffer CJ, Yoon TP. J. Am. Chem. Soc. 2007; 129: 1866
    • 4d Alexanian EJ, Lee C, Sorensen EJ. J. Am. Chem. Soc. 2005; 127: 7690
    • 5a Iglesias Á, Pérez EG, Muñiz K. Angew. Chem. Int. Ed. 2010; 49: 8109
    • 5b Sequeira FC, Turnpenny BW, Chemler SR. Angew. Chem. Int. Ed. 2010; 49: 6365
    • 5c Zhao B, Du H, Cui S, Shi Y. J. Am. Chem. Soc. 2010; 132: 3523
    • 5d Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2008; 130: 8590
    • 5e Ingalls EL, Sibbald PA, Kaminsky W, Michael FE. J. Am. Chem. Soc. 2013; 135: 8854

      For reviews on gold catalysis, see:
    • 6a Zhang L, Sun J, Kozmin SA. Adv. Synth. Catal. 2006; 348: 2271
    • 6b Fürstner A, Davies PW. Angew. Chem. Int. Ed. 2007; 46: 3410
    • 6c Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
    • 6d Hashmi AS. K, Rudolph M. Chem. Soc. Rev. 2008; 37: 1766
    • 6e Hashmi AS. K. Angew. Chem. Int. Ed. 2010; 49: 5232

    • For recent examples, see:
    • 6f Tkatchouk E, Mankad NP, Benitez D, Goddard III WA, Toste FD. J. Am. Chem. Soc. 2011; 133: 14293
    • 6g Pagar VV, Jadhav AM, Liu R.-S. J. Am. Chem. Soc. 2011; 133: 20728
    • 6h Chen Y, Chen M, Liu Y. Angew. Chem. Int. Ed. 2012; 51: 6493
    • 6i Conyers RC, Gung BW. Chem. Eur. J. 2013; 19: 654
    • 6j Liu F, Qian D, Li L, Zhao X, Zhang J. Angew. Chem. Int. Ed. 2010; 49: 6669
    • 6k Ye L, He W, Zhang L. Angew. Chem. Int. Ed. 2011; 50: 3236
    • 6l Wang D, Cai R, Sharma S, Jirak J, Thummanapelli SK, Akhmedov NG, Zhang H, Liu X, Petersen JL, Shi X. J. Am. Chem. Soc. 2012; 134: 9012
    • 6m Xu M, Ren T.-T, Li C.-Y. Org. Lett. 2012; 14: 4902
    • 6n Shu C, Liu M.-Q, Sun Y.-Z, Ye L.-W. Org. Lett. 2012; 14: 4958
    • 6o Cao Z.-Y, Wang X, Tan C, Zhao X.-L, Zhou J, Ding K. J. Am. Chem. Soc. 2013; 135: 8197
    • 6p Chen X, Chen H, Ji X, Jiang H, Yao Z.-J, Liu H. Org. Lett. 2013; 15: 1846
    • 6q Hou Q, Zhang Z, Kong F, Wang S, Wang H, Yao Z.-J. Chem. Commun. 2013; 49: 695
    • 6r Xi Y, Wang D, Ye X, Akhmedov NG, Petersen JL, Shi X. Org. Lett. 2014; 16: 306
    • 6s Ji K, Zhang L. Org. Chem. Front. 2014; 1: 34
    • 6t Yu Y.-F, Shu C, Shen C.-H, Li T.-Y, Ye L.-W. Chem. Asian J. 2013; 8: 2920
    • 6u Shu C, Liu M.-Q, Wang S.-S, Li L, Ye L.-W. J. Org. Chem. 2013; 78: 3292
    • 6v Shu C, Li L, Yu Y.-F, Jiang S, Ye L.-W. Chem. Commun. 2014; 50: 2522
  • 7 Qian J.-Q, Liu Y.-K, Zhu J, Jiang B, Xu Z.-Y. Org. Lett. 2011; 13: 4220
    • 8a Xu T, Liu G. Org. Lett. 2012; 14: 5416
    • 8b Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
    • 9a Wang X, Yao Z, Dong S, Wei F, Wang H, Xu Z. Org. Lett. 2013; 15: 2234
    • 9b Wang X, Dong S, Yao Z, Feng L, Daka P, Wang H, Xu Z. Org. Lett. 2014; 16: 22

      For halodeauration reactions, see:
    • 10a Miles DH, Veguillas M, Toste FD. Chem. Sci. 2013; 4: 3427
    • 10b Ye L, Zhang L. Org. Lett. 2009; 11: 3646
    • 10c Yu M, Zhang G, Zhang L. Org. Lett. 2007; 9: 2147
    • 11a Lin R, Ding S, Shi Z, Jiao N. Org. Lett. 2011; 13: 4498
    • 11b Nocquet-Thibault S, Retailleau P, Cariou K, Dodd RH. Org. Lett. 2013; 15: 1842
  • 12 Crystallographic data for compound 2a have been deposited with the accession numbers CCDC 980608, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
    • 13a Schuler M, Silva F, Bobbio C, Tessier A, Gouverneur V. Angew. Chem. Int. Ed. 2008; 47: 7927
    • 13b Peng Y, Cui L, Zhang G, Zhang L. J. Am. Chem. Soc. 2009; 131: 5062
    • 13c Zhang G, Peng Y, Cui L, Zhang L. Angew. Chem. Int. Ed. 2009; 48: 3112
    • 13d Wang W, Jasinski J, Hammond GB, Xu B. Angew. Chem. Int. Ed. 2010; 49: 7247
    • 13e Melhado AD, Brenzovich WE. Jr, Lackner AD, Toste FD. J. Am. Chem. Soc. 2010; 132: 8885
    • 13f de Haro T, Nevado C. J. Am. Chem. Soc. 2010; 132: 1512
    • 13g de Haro T, Nevado C. Chem. Commun. 2011; 47: 248

      For NBS-induced electrophilic cyclization, see
    • 14a Wang N, Chen B, Ma S. Adv. Synth. Catal. 2014; 356: 485
    • 14b Kothandaraman P, Koh BQ, Limpanuparb T, Hirao H, Chan PW. H. Chem. Eur. J. 2013; 19: 1978
    • 14c Kothandaraman P, Lauw SJ. L, Chan PW. H. Tetrahedron 2013; 69: 7471
    • 14d Yue D, Della CN, Larock RC. J. Org. Chem. 2006; 71: 3381
    • 14e Kesharwani T, Worlikar SA, Larock RC. J. Org. Chem. 2006; 71: 2307
  • 15 One reviewer suggested another plausible mechanism in which the reaction proceeds through sequential protodeauration and bromination to give the same products.
    • 16a Yin Y, Ma W, Chai Z, Zhao G. J. Org. Chem. 2007; 72: 5731
    • 16b Xu H.-D, Zhang R.-W, Li X, Huang S, Tang W, Hu W.-H. Org. Lett. 2013; 15: 840