Direct Gold-Catalyzed Regioselective Tetrafunctionalization of Nonactivated Alkynes

Fang Wei; Xianghua Wang; Shasha Peng; Qiuhui Jia; Chao Jiang; Shili Liu; Zhenghu Xu

doi:10.1055/s-0033-1341271

Synthesis, Table of Contents

Synthesis 2014; 46(16): 2168-2174
DOI: 10.1055/s-0033-1341271

special topic

Direct Gold-Catalyzed Regioselective Tetrafunctionalization of Nonactivated Alkynes

Fang Wei

^aKey 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

^aKey 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

^aKey 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

^aKey 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

^aKey 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

^bSchool of Medicine, Shandong University, Jinan 250012, P. R. of China

,

Zhenghu Xu*

^aKey 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

Abstract

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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.

Key words

tetrafunctionalization - alkynes - gold - catalysis - pyrroles

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References

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

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