Organic Letters
Letter
́
5498. (c) RubioMarques, P.; Rivero-Crespo, M. A.; Leyva-Perez, A.;
Scheme 6. Proposed Catalytic Cycle
Corma, A. J. Am. Chem. Soc. 2015, 137, 11832−11837. (d) Allegretti,
P. A.; Huynh, K.; Ozumerzifon, T. J.; Ferreira, E. M. Org. Lett. 2016,
18, 64−67. (e) Witham, C. A.; Huang, W.; Tsung, C. K.; Kuhn, J. N.;
Somorjai, G. A.; Toste, F. D. Nat. Chem. 2010, 2, 36−41. (f) Yamane,
Y.; Liu, X.; Hamasaki, A.; Ishida, T.; Haruta, M.; Yokoyama, T.;
Tokunaga, M. Org. Lett. 2009, 11, 5162−5165. (g) Rubio-Marqus, P.;
́
Rivero-Crespo, M. A.; Leyva-Perez, A.; Corma, A. J. Am. Chem. Soc.
́
2015, 137, 11832−11837. (h) Cook, A. K.; Coperet, C. Organo-
metallics 2018, 37, 1342−1345. (i) Li, B.; Ju, Z.; Zhou, M.; Su, K.;
Yuan, D. Angew. Chem., Int. Ed. 2019, 58, 7687−7691.
(2) (a) Qu, C. H.; Zhang, S.; Du, H.; Zhu, C. Chem. Commun. 2016,
52, 14400−14403. (b) Ilies, L.; Isomura, M.; Yamauchi, S.-i.;
Nakamura, T.; Nakamura, E. J. Am. Chem. Soc. 2017, 139, 23−26.
(c) Watanabe, T.; Mutoh, Y.; Saito, S. J. Am. Chem. Soc. 2017, 139,
7749−7752.
(3) (a) Hirner, J. J.; Faizi, D. J.; Blum, S. A. J. Am. Chem. Soc. 2014,
136, 4740−4745. (b) Chong, E.; Blum, S. A. J. Am. Chem. Soc. 2015,
137, 10144−10147. (c) Issaian, A.; Tu, K. N.; Blum, S. A. Acc. Chem.
Res. 2017, 50, 2598−2609.
example of using rhenium as a π acid catalyst, by which novel
branch selectivities were demonstrated compared to the
previously reported linear selectivities of the platinum catalyst.
Controlled experiments supported a concerted [3,3]-sigma-
tropic rearrangement other than a carbocation shift mecha-
nism.17 Further work on the asymmetry of this reaction and
detailed mechanistic studies are currently underway in our
laboratory.
(4) (a) Monteiro, N.; Balme, G. Synlett 1998, 1998, 746−747.
(b) Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis
2003, 2003, 2115−2134.
(5) Fu
15025. Fu
̈
rstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024−
rstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127,
̈
15024−15025.
(6) For reviews, see: (a) Kuninobu, Y.; Takai, K. Chem. Rev. 2011,
111, 1938−1953. (b) Hua, R.; Jiang, J.-L. Curr. Org. Synth. 2007, 4,
151−174.
ASSOCIATED CONTENT
* Supporting Information
■
S
(7) (a) Mao, G.; Huang, Q.; Wang, C. Eur. J. Org. Chem. 2017, 2017,
3549−3564. (b) Fukumoto, Y.; Daijo, M.; Chatani, N. J. Am. Chem.
Soc. 2012, 134, 8762−8765. (c) Hori, S.; Murai, M.; Takai, K. J. Am.
Chem. Soc. 2015, 137, 1452−1457. (d) Iwasawa, N.; Watanabe, S.;
Ario, A.; Sogo, H. J. Am. Chem. Soc. 2018, 140, 7769−7772. (e) Xia,
D.; Wang, Y.; Du, Z.; Zheng, Q.-Y.; Wang, C. Org. Lett. 2012, 14,
588−591. (f) Murai, M.; Uemura, E.; Hori, S.; Takai, K. Angew.
Chem., Int. Ed. 2017, 56, 5862−5866. (g) Murai, M.; Uemura, E.;
Hori, S.; Takai, K. Angew. Chem., Int. Ed. 2017, 56, 5862−5866.
The Supporting Information is available free of charge on the
Experimental details and complete analytical data (PDF)
Accession Codes
CCDC 1914271 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
(8) For selective reviews of alkyne activation, see: (a) Furstner, A.
̈
́
́
̃
ez, E.;
Chem. Soc. Rev. 2009, 38, 3208−3221. (b) Jimenez-Nun
Echavarren, A. M. Chem. Rev. 2008, 108, 3326−3350. (c) Marion, N.;
Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776−1782. (d) Hashmi, A. S.
K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766−1775. (e) Gorin, D.
J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351−3378.
AUTHOR INFORMATION
■
́
(f) Corma, A.; Leyva-Perez, A.; Sabater, M. J. Chem. Rev. 2011, 111,
Corresponding Author
ORCID
1657−1712. (g) Bandini, M. Chem. Soc. Rev. 2011, 40, 1358−1367.
(h) Zi, W.; Toste, F. D. Chem. Soc. Rev. 2016, 45, 4567−4589.
(9) For rhenium as a π acid catalyst, see: (a) Kusama, H.; Yamabe,
H.; Onizawa, Y.; Hoshino, T.; Iwasawa, N. Angew. Chem., Int. Ed.
2005, 44, 468−470. (b) Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc.
2003, 125, 15760−15761.
Notes
(10) For our studies of alkyne activation, see: (a) Zheng, Y.; Zi, W.
Tetrahedron Lett. 2018, 59, 2205−2213. (b) Wang, H. F.; Wang, S. Y.;
Qin, T. Z.; Zi, W. Chem. - Eur. J. 2018, 24, 17911−17914. (c) Zheng,
Y.; Guo, L.; Zi, W. Org. Lett. 2018, 20, 7039−7043. (d) Rong, M.-G.;
Qin, T.-Z.; Liu, X.-R.; Wang, H.-F.; Zi, W. Org. Lett. 2018, 20, 6289−
6293.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the National “Young Thousand
Talents Plan”, the National Natural Science Foundation of
China (21871150), and the Fundamental Research Funds for
the Central Universities. The authors gratefully acknowledge
the State Key Laboratory of Elemento-organic Chemistry and
the College of Chemistry of Nankai University for generous
start-up financial support.
(11) For selective reviews of [3,3]-sigmatropic rearrangements, see:
(a) Martín Castro, A. M. Chem. Rev. 2004, 104, 2939−3002.
(b) Majumdar, K. C.; Alam, S.; Chattopadhyay, B. Tetrahedron 2008,
64, 597−643. (c) Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Chem. Soc.
Rev. 2009, 38, 3133−3148. (d) Jones, A. C.; May, J. A.; Sarpong, R.;
Stoltz, B. M. Angew. Chem., Int. Ed. 2014, 53, 2556−2591.
(12) For selective examples of charge-accelerated [3,3]-sigmatropic
rearrangements, see: (a) Yoon, T. P.; Dong, V. M.; MacMillan, D. W.
J. Am. Chem. Soc. 1999, 121, 9726−9727. (b) Valerio, V.; Madelaine,
C.; Maulide, N. Chem. - Eur. J. 2011, 17, 4742−4745. (c) Eberhart, A.
J.; Cicoira, C.; Procter, D. J. Org. Lett. 2013, 15, 3994−3997.
REFERENCES
■
̈
(1) (a) Perea-Buceta, J. E.; Wirtanen, T.; Laukkanen, O.-V.; Makela,
M. K.; Nieger, M.; Melchionna, M.; Huittinen, N.; Lopez-Sanchez, J.
A.; Helaja, J. Angew. Chem., Int. Ed. 2013, 52, 11835−11839.
(b) Kumaran, E.; Leong, W. K. Tetrahedron Lett. 2014, 55, 5495−
́
(d) Shrives, H. J.; Fernandez-Salas, J. A.; Hedtke, C.; Pulis, A. P.;
D
Org. Lett. XXXX, XXX, XXX−XXX