Gold-Catalyzed Intermolecular CS Bond Formation: Efficient Synthesis of α-Substituted Vinyl Sulfones†
Yumeng Xi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorBoliang Dong
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorEdward J. McClain
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorQiaoyi Wang
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorTesia L. Gregg
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorDr. Novruz G. Akhmedov
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorProf. Jeffrey L. Petersen
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorCorresponding Author
Prof. Xiaodong Shi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/===Search for more papers by this authorYumeng Xi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorBoliang Dong
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorEdward J. McClain
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorQiaoyi Wang
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorTesia L. Gregg
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorDr. Novruz G. Akhmedov
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorProf. Jeffrey L. Petersen
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorCorresponding Author
Prof. Xiaodong Shi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/===Search for more papers by this authorWe are grateful to the NSF (CAREER-CHE-0844602 and CHE-1228336) and the NSFC (21228204) for financial support.
Abstract
A general method for the synthesis of α-substituted vinyl sulfones makes use of a combination of a triazole gold complex and gallium triflate. This efficient CS bond formation between simple terminal alkynes and sulfinic acids provides access to various α-substituted vinyl sulfones.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange_201310142_sm_miscellaneous_information.pdf44.9 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aA. Vigalok, CX Bond Formation, Springer, Heidelberg, 2010;
- 1bA. K. Yudin, Catalyzed Carbon-Heteroatom Bond Formation, Wiley-VCH, Weinheim, 2012;
- 1cH. Liu, X. Jiang, Chem. Asian J. 2013, 8, 2546.
- 2
- 2aJ. T. Palmer, D. Rasnick, J. L. Klaus, D. Bromme, J. Med. Chem. 1995, 38, 3193;
- 2bM. M. M. Santos, R. Moreira, Mini-Rev. Med. Chem. 2007, 7, 1040;
- 2cI. D. Kerr, J. H. Lee, C. J. Farady, R. Marion, M. Rickert, M. S. Kailash, C. Pandey, C. R. Caffrey, J. Legac, E. Hansell, J. H. McKerrow, C. S. Craik, P. J. Rosenthal, L. S. Brinen, J. Biol. Chem. 2009, 284, 25697;
- 2dA. F. Kisselev, W. A. van der Linden, H. S. Overkleeft, Chem. Biol. 2012, 19, 99;
- 2eL. Ni, X. S. Zheng, P. K. Somers, L. K. Hoong, R. R. Hill, E. M. Marino, K.-L. Suen, U. Saxena, C. Q. Meng, Bioorg. Med. Chem. Lett. 2003, 13, 745.
- 3
- 3aJ. Morales-Sanfrutos, J. Lopez-Jaramillo, M. Ortega-Munoz, A. Megia-Fernandez, F. Perez-Balderas, F. Hernandez-Mateo, F. Santoyo-Gonzalez, Org. Biomol. Chem. 2010, 8, 667;
- 3bF. J. Lopez-Jaramillo, F. Hernandez-Mateo, F. Santoyo-Gonzalez, Integrative Proteomics (Ed.: ), InTech, Rijeka, 2012, pp. 301–327.
- 4
- 4aV. Nair, A. Augustine, T. D. Suja, Synthesis 2002, 2259;
- 4bD. C. Meadows, J. Gervay-Hague, Med. Res. Rev. 2006, 26, 793;
- 4cH. Qian, X. Huang, Synlett 2001, 1913;
- 4dX. Huang, D. Duan, W. Zheng, J. Org. Chem. 2003, 68, 1958;
- 4eW. M. Xu, E. Tang, X. Huang, Synthesis 2004, 2094;
- 4fD. Díez, P. García, I. S. Marcos, N. M. Garrido, P. Basabe, H. B. Broughton, J. G. Urones, Tetrahedron 2005, 61, 699;
- 4gZ.-H. Guan, W. Zuo, L.-B. Zhao, Z.-H. Ren, Y.-M. Liang, Synthesis 2007, 1465;
- 4hG. Signore, C. Malanga, R. Menicagli, Tetrahedron 2008, 64, 11218;
- 4iB. Das, M. Lingaiah, K. Damodar, N. Bhunia, Synthesis 2011, 2941;
- 4jS. Liang, R.-Y. Zhang, G. Wang, S.-Y. Chen, X.-Q. Yu, Eur. J. Org. Chem. 2013, 7050.
- 5
- 5aJ. M. Baskin, Z. Wang, Org. Lett. 2002, 4, 4423;
- 5bV. Nair, A. Augustine, T. G. George, L. G. Nair, Tetrahedron Lett. 2001, 42, 6763;
- 5cS. Cacchi, G. Fabrizi, A. Goggiamani, L. M. Parisi, R. Bernini, J. Org. Chem. 2004, 69, 5608;
- 5dA. Battace, T. Zair, H. Doucet, M. Santelli, Synthesis 2006, 3495;
- 5eF. Huang, R. A. Batey, Tetrahedron 2007, 63, 7667;
- 5fM. Bian, F. Xu, C. Ma, Synthesis 2007, 2951;
- 5gD. C. Reeves, S. Rodriguez, H. Lee, N. Haddad, D. Krishnamurthy, C. H. Senanayake, Tetrahedron Lett. 2009, 50, 2870;
- 5hQ.-L. Xu, L.-X. Dai, S.-L. You, Org. Lett. 2010, 12, 800;
- 5iN. Taniguchi, Synlett 2011, 1308;
- 5jN. Taniguchi, Synlett 2012, 1245.
- 6Radical intermediates favor anti-Markovnikov addition; see Ref. [5i] and: Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang, A. Lei, J. Am. Chem. Soc. 2013, 135, 11481.
- 7
- 7aR. Chawla, R. Kapoor, A. K. Singh, L. D. S. Yadav, Green Chem. 2012, 14, 1308;
- 7bJ. W. Lee, C.-W. Lee, J. H. Jung, D. Y. Oh, Synth. Commun. 2000, 30, 2897;
- 7cK. Inomata, S.-i. Sasaoka, T. Kobayashi, Y. Tanaka, S. Igarashi, T. Ohtani, H. Kinoshita, H. Kotake, Bull. Chem. Soc. Jpn. 1987, 60, 1767;
- 7dK. Inomata, T. Kobayashi, S.-i. Sasaoka, H. Kinoshita, H. Kotake, Chem. Lett. 1986, 15, 289;
- 7eJ. B. Hendrickson, P. S. Palumbo, Tetrahedron Lett. 1985, 26, 2849;
- 7fC.-N. Hsiao, H. Shechter, Tetrahedron Lett. 1982, 23, 3455;
- 7gT. G. Back, S. Collins, J. Org. Chem. 1981, 46, 3249;
- 7hH. Kotake, K. Inomata, M. Sumita, Chem. Lett. 1978, 7, 717;
- 7iS. Chodroff, W. Whitmore, J. Am. Chem. Soc. 1950, 72, 1073.
- 8
- 8aA. S. K. Hashmi, F. D. Toste, Modern Gold Catalyzed Synthesis, Wiley-VCH, Weinheim, 2012;
10.1002/9783527646869 Google Scholar
- 8bA. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2012, 41, 2448;
- 8cD. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351;
- 8dA. Arcadi, Chem. Rev. 2008, 108, 3266;
- 8eE. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326;
- 8fR. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382;
- 8gA. S. K. Hashmi, Chem. Rev. 2007, 107, 3180;
- 8hA. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478;
10.1002/ange.200604335 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 3410;
- 8iL. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271;
- 8jA. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064;
10.1002/ange.200602454 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 7896.
- 9
- 9aN. Morita, N. Krause, Angew. Chem. 2006, 118, 1930;
10.1002/ange.200503846 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 1897;
- 9bI. Nakamura, T. Sato, Y. Yamamoto, Angew. Chem. 2006, 118, 4585–4587; Angew. Chem. Int. Ed. 2006, 45, 4473–4475;
- 9cP. W. Davies, S. J. C. Albrecht, Chem. Commun. 2008, 238;
- 9dI. Nakamura, T. Sato, M. Terada, Y. Yamamoto, Org. Lett. 2008, 10, 2649;
- 9eL. L. Santos, V. R. Ruiz, M. J. Sabater, A. Corma, Tetrahedron 2008, 64, 7902;
- 9fA. Aponick, C.-Y. Li, J. Malinge, E. F. Marques, Org. Lett. 2009, 11, 4624;
- 9gX. Zhao, Z. Zhong, L. Peng, W. Zhang, J. Wang, Chem. Commun. 2009, 2535;
- 9hP. W. Davies, S. J. C. Albrecht, Angew. Chem. 2009, 121, 8522;
10.1002/ange.200904309 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 8372;
- 9iM. Jean, J. Renault, P. van de Weghe, N. Asao, Tetrahedron Lett. 2010, 51, 378;
- 9jR. J. Mudd, P. C. Young, J. A. Jordan-Hore, G. M. Rosair, A.-L. Lee, J. Org. Chem. 2012, 77, 7633;
- 9kA. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657.
- 10P. C. Young, S. L. J. Green, G. M. Rosair, A.-L. Lee, Dalton Trans. 2013, 42, 9645.
- 11For representative examples, see:
- 11aN. D. Shapiro, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 4160;
- 11bG. Li, L. Zhang, Angew. Chem. 2007, 119, 5248; Angew. Chem. Int. Ed. 2007, 46, 5156;
- 11cC.-W. Li, K. Pati, G.-Y. Lin, H.-H. Hung, R.-S. Liu, Angew. Chem. 2010, 122, 10087; Angew. Chem. Int. Ed. 2010, 49, 9891;
- 11dB. Lu, Y. Li, Y. Wang, D. H. Aue, Y. Luo, L. Zhang, J. Am. Chem. Soc. 2013, 135, 8512.
- 12D. De Filippo, F. Momicchioli, Tetrahedron 1969, 25, 5733.
- 13
- 13aB. C. Chary, S. Kim, J. Org. Chem. 2010, 75, 7928;
- 13bT. Luo, M. Dai, S. L. Zheng, S. L. Schreiber, Org. Lett. 2011, 13, 2834;
- 13cM. R. Kuram, M. Bhanuchandra, A. K. Sahoo, J. Org. Chem. 2010, 75, 2247;
- 13dP. H. Lee, S. Kim, A. Park, B. C. Chary, S. Kim, Angew. Chem. 2010, 122, 6958; Angew. Chem. Int. Ed. 2010, 49, 6806. Sulfonic acids are also suitable substrates for such addition reactions; see:
- 13eD.-M. Cui, Q. Meng, J.-Z. Zheng, C. Zhang, Chem. Commun. 2009, 1577.
- 14L. Ye, W. He, L. Zhang, Angew. Chem. 2011, 123, 3294; Angew. Chem. Int. Ed. 2011, 50, 3236.
- 15
- 15aH. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc. 2009, 131, 12100;
- 15bY. Chen, W. Yan, N. G. Akhmedov, X. Shi, Org. Lett. 2010, 12, 344;
- 15cD. Wang, X. Ye, X. Shi, Org. Lett. 2010, 12, 2088;
- 15dD. Wang, L. N. S. Gautam, C. Bollinger, A. Harris, M. Li, X. Shi, Org. Lett. 2011, 13, 2618;
- 15eQ. Wang, S. Aparaj, N. G. Akhmedov, J. L. Petersen, X. Shi, Org. Lett. 2012, 14, 1334;
- 15fD. Wang, R. Cai, S. Sharma, J. Jirak, S. K. Thummanapelli, N. G. Akhmedov, H. Zhang, X. Liu, J. L. Petersen, X. Shi, J. Am. Chem. Soc. 2012, 134, 9012;
- 15gY. Xi, B. Dong, X. Shi, Beilstein J. Org. Chem. 2013, 9, 2537;
- 15hY. Yu, W. Yang, F. Rominger, A. S. K. Hashmi, Angew. Chem. 2013, 125, 7735; Angew. Chem. Int. Ed. 2013, 52, 7586;
- 15iY. Xi, D. Wang, X. Ye, N. G. Akhmedov, J. L. Petersen, X. Shi, Org. Lett. 2014, 16, 306;
- 15jY. Xi, Q. Wang, Y. Su, M. Li, X. Shi, Chem. Commun. 2014, 50, 2158;
- 15kQ. Wang, S. E. Motika, N. G. Akhmedov, J. L. Petersen, X. Shi, Angew. Chem. 2014, DOI: ; Angew. Chem. Int. Ed. 2014, DOI: .
- 16See Ref. [15i]. According to our previous observations, the role of gallium triflate involves coordination to the triazole ligand, which frees the cationic gold complex.
- 17The α,β-diaryl and α-aryl-β-alkyl alkynes gave complex reaction mixtures, which is presumably due to the decomposition of sulfinic acid at higher temperatures. The α,β-dialkyl alkynes gave some products, the structures of which could not be identified yet (but they are not the desired vinyl sulfones).
- 18CCDC 966046 (3 bh) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 19
- 19aJ.-E. Bäckvall, R. Chinchilla, C. Najera, M. Yus, Chem. Rev. 1998, 98, 2291;
- 19bT. G. Back, K. N. Clary, D. Gao, Chem. Rev. 2010, 110, 4498.
- 20
- 20aJ.-E. Baeckvall, S. K. Juntunen, J. Am. Chem. Soc. 1987, 109, 6396;
- 20bT.-S. Chou, S.-C. Hung, J. Org. Chem. 1988, 53, 3020;
- 20cR. F. de la Pradilla, C. Montero, M. Tortosa, A. Viso, Chem. Eur. J. 2005, 11, 5136.
- 21T. G. Back, M. Parvez, H. Zhai, J. Org. Chem. 2003, 68, 9389.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.