Chemistry - A European Journal
10.1002/chem.202002696
FULL PAPER
[
9] X. Huang, L. Zhang, J. Am. Chem. Soc. 2007, 129, 6398-6399. For key
reviews on homogeneous gold catalysis, see: a) D. Pflaesterer, A. S. K.
Hashmi, Chem. Soc. Rev., 2016, 45, 1331-1367. b) A. S. K. Hashmi,
Chem. Rev., 2007, 107, 3180-3211. c) A. S. K. Hashmi, G. J. Hutchings,
Angew. Chem. Int. Ed., 2006, 45, 7896-7936.
B. Y. thanks the China Scholarship Council for Ph.D grant. I.C.
and A.P thank the European Research Council (ERC) for funding
under the European Union’s Horizon 2020 research and
innovation programme (grant agreement No 648558, STRIGES
CoG grant). We would like to thank Pr. P. Belmont for fruitful
discussions and single-cristal X-ray diffraction service from
ICMMO-UMR8182 Orsay.
[10] G. Zhang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 12598-12599.
[
11] J. T. Binder, B. Crone, T. T. Haug, H. Menz, S. F. Kirsch, Org. Lett.,
008, 10, 1025-1028 For a highlight on the combination of gold
2
.
catalysis and organocatalysis, see: A. S. K. Hashmi, C. Hubbert, Angew.
Chem. Int. Ed., 2010, 49, 1010-1012.
Keywords: Allenyl silver • dihydrofuran • isomerization •
[
[
[
12] Z. Zhang, Q. Zhang, Z. Ni, Q. Liu, Chem. Commun., 2010, 46, 1269-
1271.
intramolecular cyclization
13] Z. Zhang, S. Fang, Q. Liu, G. Zhang, Adv. Synth. Catal., 2012, 354,
9
27-932.
14] H. Westmijze, H. Kleijn, H.J.T. Bos, P. Vermeer, J. Organomet. Chem.,
980, 199, 293-297. b) H. Westmijze, K. Ruitenberg, .I. Meijer, P.
[
[
1] T. G. Kilroy, T. P. O’Sullivan, P. J. Guiry, Eur. J. Org. Chem., 2005, 23,
929–4949.
4
1
2] B. H. Lipshutz, Chem. Rev., 1986, 86, 795−819. b) B. M. Fraga, Nat.
Prod. Rep., 1992, 9, 217−241. c) A. T. Merritt, S. B. Ley, Clerodane,
Nat. Prod. Rep., 1992, 9, 243−287. d) M. M. Faul, B. E. Huff, Chem.
Rev., 2000, 100, 2407−2474. e) M. C. Elliott, J. Chem. Soc. Perkin
Trans. 1, 2002, 2301−2323. f) F. Garzino, A. Mꢀou, P. Brun, Synthesis,
Vermeer, Tetrahedron. Lett., 1980, 21, 1771-1772. c) J. Meijer, K.
Ruitenberg, H. Westmijze, P. Vermeer, Synthesis, 1981, 551-554.
15] For recent results on silver-catalyzed conversions of alkynes, see:
a) S. Dabral, U. Licht, P. Rudolf, G. Bollmann, A. S. K. Hashmi, T.
Schaub, Green Chem., 2020, 22, 1553-1558. b) A. Ahrens, N. F.
Heinrich, S. R. Kohl, M. Hokamp, M. Rudolph, F. Rominger, A. S. K.
Hashmi, Adv. Synth. Catal., 2019, 361, 5605-5615. c) Y.-Y Yang, P.
Antoni, M. Zimmer, K. Sekine, F.F. Mulks, L. Hu, L. Zhang, M. Rudolph,
F. Rominger, A.S.K. Hashmi, Angew. Chem. Int. Ed., 2019, 58, 5129-
[
2
003, 0598−0602. g) T. G. Kilroy, T. P. O’Sullivan, P. J. Guiry, Eur. J.
Org. Chem., 2005, 4929−4949. (h) R. A. Brawn, J. S. Panek, Org. Lett.,
010, 12, 4624-4627.
3] For some reactions using chiral auxiliaries and precursors, see: a) H. J.
Gais, L. R. Reddy, G. S Babu, G. Raabe, J. Am. Chem. Soc., 2004
26, 4859−4864. b) W. Xia, C. Yang, B. O. Patrick, J. R. Scheffer, C.
2
[
[
,
5
133. d) S. Dabral, B. Bayarmagnai, M. Hermsen, J. Schießl, V. Mormul,
1
A. S. K. Hashmi, T. Schaub, Org. Lett., 2019, 21, 1422-1425. e) F. Chen,
A. S. K. Hashmi, Org. Lett., 2016, 18, 2880-2882.
Scott, J. Am. Chem. Soc., 2005, 127, 2725−2730. c) R. K. Bowman, J.
S. Johnson, Org. Lett., 2006, 8, 573−576. d) J.-C. Zheng, C.-Y. Zhu, X.-
L. Sun, Y. Tang, L.-X. Dai, J. Org. Chem., 2008, 73, 6909−6912.
[
16] For selected Ag catalysed Glaser-Hay coupling, see: a) Y.-Q. Zhang,
N. Kepčija, M. Kleinschrodt, K. Diller, S. Fischer, A. C. Papageorgiou,
F. Allegretti, J. Björk, S. Klyatskaya, F. Klappenberger, M. Ruben, J. V.
Barth, Nat. Commun., 2012, 3, 1286–1293. b) H.-Y. Gao, H. Wagner,
4] For some metal-mediated cyclization reactions, see: a) H. M. L. Davies,
G. Ahmed, R. L. Calvo, M. R. Churchill, D. G. Churchill, J. Org. Chem.,
1
998, 63, 2641−2645. b) D. A. Evans, Z. K. Sweeney, T. Rovis, J. S.
D.-Y. Zhong, J.-H. Franke, A. Studer, H. Fuchs, Angew. Chem., 2013
2, 4024–4028. c) H.-Y. Gao, H. Wagner, D.-Y. Zhong, J.-H. Franke, A.
Studer, H. Fuchs, Angew. Chem. Int. Ed., 2013, 125, 4116–4120.
17] Crystallographic data are available from the Cambridge
Crystallographic Data Centre: a) Compound , reference CCDC no.
972313. b) Compound 6g reference CCDC no. 1972314. c)
,
Tedrow, J. Am. Chem. Soc., 2001, 123, 12095−12096. c) S. Son, G. C.
Fu, J. Am. Chem. Soc., 2007, 129, 1046−1047. d) J.-L. Zhou, L.-J.
Wang, H. Xu, X.-L. Sun, Y. Tang, ACS. Catal., 2013, 3, 685−688. e) D.
Sinha, A. Biswas, V. K. Singh, Org. Lett., 2015, 17, 3302−3305. f) Y.
Zhou, F.-L. Zhu, Z.-T. Liu, X.-M. Zhou, X.-P. Hu, Org. Lett., 2016, 18,
5
[
3
1
,
2
734−2737. g) J. Reece, P. Ritashree, A. P. Nicholas, C. E. Sear, P. W.
Smith, A. Ribaucourt, D. M. Hodgson, Org. Biomol. Chem., 2016, 14,
875–5893. h) O. El-Sepelgy, A. Brzozowska, J. Sklyaruk, Y. K. Jang,
Compound 6h, reference CCDC no. 1972315.
18] Only traces of 2d along with degradation products were observed by 1
H
[
[
[
5
NMR
V. Zubar, M. Rueping, Org. Lett., 2018, 20, 696-699.
19] A. Vitérisi, A. Orsini, J-M. Weibel, P. Pale, Tett. Lett., 2006, 47, 2779-
781.
20] U. Létinois-Halbes, P. Pale, S. Berger, J. Org. Chem., 2005, 70, 9185-
190.
[
[
[
5] For some organocatalytic reactions, see: a) R.-Q. Mei, X.-Y. Xu, L.
Peng, F. Wang, F. Tian, L.-X. Wang, Org. Biomol. Chem., 2013, 11,
2
1
286−1289. b) N.-J. Zhong, F. Wei, Q.-Q. Xuan, L. Liu, D. Wang, Y.-J.
9
Chen, Chem. Commun., 2013, 49, 11071−11073. c) M. A. Calter, A.
Korotkov, Org. Lett., 2015, 17, 1385−1388. d) Y. Cheng, Y. Han, P. Li,
Org. Lett., 2017, 19, 4774-4777.
[
[
[
23] For such cycloetherification mediated by silver see for example: B.
Alcaide, P. Almendros, T. Martinez del Campo, R. Carrascosa, Eur. J.
Org. Chem. 2010, 4912–4919.
6] For some representatives [3+2] reactions, see : a) J. Tsuji, I. Watanabe,
I. Minami, I. Shimizu, J. Am. Chem. Soc., 1985, 107, 2196-2198. b) I.
Minami, M. Yuhara, I. Watanabe, J. Tsuji, J. Organomet. Chem., 1987
,
3
34, 225-242. c) F.-L. Zhu, Y.-H. Wang, D.-Y. Zhang, J. Xu, X.-P. Hu,
Angew. Chem. Int. Ed., 2014, 53, 10223−10227. d) Y. Zhou, F. -L. Zhu,
Z.-T. Liu, X.-M. Zhou, X.-P. Hu, Org. Lett., 2016, 18, 2734-2737.
7] For selected reviews, see: a) T. Hashimoto, K. Maruoka, Chem. Rev.,
2
018, 115, 5366-5412. b) L. M. Stanley, M.P. Sibi, Chem. Rev., 2008
,
1
18, 2887-2902. c) H. Pélissier, Tetrahedron, 2007, 63, 3235-3285. d)
V. Nair, T. D. Suja, Tetrahedron, 2007, 63, 12247-12275. e) K. Harju,
J. Yli-Kauhaluoma, Mol. Divers., 2005, 9, 187-207. f) K. V. Gothelf K. A.
Jørgensen, Chem. Rev., 1998, 98, 863-909. g) M. S. Singh, S.
Chowdhury, S. Koley, Tetrahedron, 2016, 72, 1603-1644. h) C. Nájera,
J. M. Sansano, J. Organomet. Chem., 2014, 771, 78-92.
[
8] For selected reviews and books, see: a) D. M. T. Chan, in
Comprehensive Organic Synthesis 1st ed. (Eds.: B. M. Trost, I.
Fleming), Pergamon, Oxford, New York, 1991, pp. 271-314. b) N.
Iwasawa, in Comprehensive Organic Synthesis 2nd ed. (Eds.: P.
Knochel, G. A. Molander), Elsevier, Oxford, New York, 2014, pp. 273-
3
50. c) S. Yamago, E. Nakamura, Org. React., 2002, 61, 1-217. d) P.
Le Marquand, W. Tam, Angew. Chem. Int. Ed., 2008, 47, 2926-2928.
e) M. E. Welker, Chem. Rev. 1992, 92 97-112
,
.
6
This article is protected by copyright. All rights reserved.