Page 9 of 11
Journal of the American Chemical Society
We thank MINECO/FEDER, UE (CTQ2016-75960-P),
1
2
3
4
5
6
7
MINECO-Severo Ochoa Excellence Acreditation 2014-2018,
SEV-2013-0319 and Severo Ochoa predoctoral fellowship to
M. E. O), European Research Council (Advanced Grant No.
321066), AGAUR (2014 SGR 818), and CERCA Program / Gen-
eralitat de Catalunya for financial support. We also thank the
ICIQ X-ray diffraction unit for the X-ray structures.
Baumann, A. N.; Kiefl, G. M.; Emmerling, S. T.; Didier, D. Chem.
Eur. J. 2017, 23, 1634–1644.
(9) (a) Yang, C.; Inoue, Y. Chem. Soc. Rev. 2014, 43, 4123−4143.
(b) Brimioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew.
Chem., Int. Ed. 2015, 54, 3872−3890. (c) Xu, Y.; Conner, M. L.;
Brown, M. K. Angew. Chem Int. Ed. 2015, 54, 11918−11928. (d)
Blum, T. R.; Miller, Z. D.; Bates, D. M.; Guzei, I. A.; Yoon, T. P.
Science 2016, 354, 1391–1395. (e) Tröster, A.; Alonso, R.; Bauer, A.;
Bach, T. J. Am. Chem. Soc. 2016, 138, 7808−7811. (f) Poplata, S.;
Tröster, A.; Zou, Y.-Q.; Bach, T. Chem. Rev. 2016, 116, 9748–9815.
8
9
REFERENCES
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(1) (a) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008,
108, 3326-3350. (b) Obradors, C.; Echavarren, A. M. Acc. Chem.
Res. 2014, 47, 902−912. (c) Dorel, R.; Echavarren, A. M. Chem.
Rev. 2015, 115, 9028–9072.
(10) (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96,
49–92. (b) Xu, Y.; Conner, M. L.; Brown, M. K. Angew. Chem. Int.
Ed. 2015, 54, 11918–11928. (c) Fructos, M. R.; Prieto, A. Tetrahe-
dron 2016, 72, 355–369.
(2) (a) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208–3221. (b)
Fürstner, A. Acc. Chem. Res. 2014, 47, 925–938. (c) Zhang, Y.;
Luo, T.; Yang, Z. Nat. Prod. Rep. 2014, 31, 489–503. (d) Pflästerer,
D.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 1331–1367. (e)
Stathakis, C. I.; Gkizis, P. L.; Zografos, A. L. Nat. Prod. Rep. 2016,
33, 1093–1117.
(11) (a) The cobalt(I)-catalyzed reaction of 1,3-enynes shows a
broader scope, leading to cyclobutenes with a variety of styrenes
and other terminal alkenes: Nishimura, A.; Tamai, E.; Ohashi,
M.; Ogoshi, S. Chem. Eur. J. 2014, 20, 6613–6617. (b) Ni(0)-
catalyzed reaction of 1,3-enynes to form cyclobutenes: Nishi-
mura, A.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2012, 134,
15692–15695.
(3) (a) López-Carrillo, V.; Echavarren, A. M. J. Am. Chem. Soc.
2010, 132, 9292–9294. (b) de Orbe, M. E.; Echavarren, A. M. Org.
Synth. 2016, 93, 115–126.
(12) Sakai, K.; Kochi, T.; Kakiuchi, F. Org. Lett. 2013, 15, 1024–
(4) Homs, A.; Obradors, C.; Leboeuf, D.; Echavarren, A. M.
1027.
Adv. Synth. Catal. 2014, 356, 221–228.
(13) Motokura, K.; Nakayama, K.; Miyaji, A.; Baba, T. Chem-
CatChem 2011, 3, 1419–1421.
(5) Obradors, C.; Leboeuf, D.; Aydin, J.; Echavarren, A. M.
Org. Lett. 2013, 15, 1576–1579.
(14) (a) T. Shibata, K. Takami, A. Kawachi, Org. Lett. 2006, 8,
1343–1345. (b) Kossler, D.; Cramer, N. Chem. Sci. 2017, 8, 1862–1866.
(6) Ranieri, B.; Obradors, C.; Mato, M.; Echavarren, A. M. Org.
Lett. 2016, 18, 1614–1617.
(15) Tam, W.; Goodreid, J. Cockburn, N. Curr. Org. Synt. 2009,
6, 219–238.
(7) (a) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449–
1484. (b) Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103,
1485–1538. (c) Luparia, M.; Audisio, D.; Maulide, N. Synlett. 2011,
735–740. (d) Misale, A.; Niyomchon, S.; Maulide, N. Acc. Chem.
Res. 2016, 49, 2444–2458.
(16) (a) Jordan, R. W.; Tam, W. Org. Lett. 2000, 2, 3031–3034.
(b) Huang, D.-J.; Rayabarapu, D. K.; Li, L.-P.; Sambaiah, T.;
Cheng, C.-H. Chem. Eur. J. 2000, 6, 3706–3713. (c) Chao, K. C.;
Rayabarapu, D. K.; Wang, C.-C.; Cheng, C-H. J. Org. Chem. 2001,
66, 8804–8810. (d) Alvarez, P.; Gimeno, J.; Lastra, E.; García-
Granda, S.; Van der Maelen, J. F.; Bassetti, M. Organometallics
2001, 20, 3762–3771. (c) Treutwein, J.; Hilt, G. Angew. Chem. Int.
Ed. 2008, 47, 6811–6813. (d) Fan, B.-M.; Li, X.-J.; Peng, F.-Z.;
Zhang, H.-B.; Chan, A. S. C.; Shao, Z.-H. Org. Lett. 2010, 12, 304–
306. (e) Hilt, G.; Paul, A.; Treutwein, J. Org. Lett. 2010, 12, 1536–
1539.
(8) (a) Masarwa, A.; Fürstner, A.; Marek, I. Chem. Commun.
2009, 5760–5762. (b) Liu, R.; Zhang, M.; Wyche, T. P.; Winston-
McPherson, G. N.; Bugni, T. S.; Tang, W. Angew. Chem. Int. Ed.
2012, 51, 7503–7506. (c) Niyomchon, S.; Audisio, D.; Luparia, M.;
Maulide, N. Org. Lett. 2013, 15, 2318–2321. (d) Souris, C.; Misale,
A.; Chen, Y.; Luparia, M.; Maulide, N. Org. Lett. 2015, 17, 4486–
4489. (e) Chen, Y.-J.; Hu, T.-J.; Feng, C.-G.; Lin, G.-Q. Chem.
Commun. 2015, 51, 8773–8776. (f) Eisold, M.; Didier, D. Angew.
Chem. Int. Ed. 2015, 54, 15884–15887. (g) Guisán-Ceinos, M.;
Parra, A.; Martín-Heras, V.; Tortosa, M. Angew. Chem. Int. Ed.
2016, 55, 6969–6972. (h) Mercer, J. A. M.; Cohen, C. M.; Shuken,
S. R.; Wagner, A. M.; Smith, M. W.; Moss, F. R., III; Smith, M. D.;
Vahala, R.; Gonzalez-Martinez, A.; Boxer, S. G.; Burns, N. Z. J.
Am. Chem. Soc. 2016, 138, 15845–15848. (i) Roy, S. R.; Eijsberg, H.;
Bruffaerts, J.; Marek, I. Chem. Sci. 2017, 8, 334–339. (j) Eisold, M.;
(17) (a) Snider, B. B.; Rodini, D. J.; Conn, R. S. E.; Sealfon, S. J.
Am. Chem. Soc. 1979, 101, 5283–5293. (b) Snider, B. B. Acc. Chem.
Res. 1980, 13, 426–432. (c) Okamoto, K.; Shimbayashi, T.; Tamu-
ra, E.; Ohe, K. Org. Lett. 2015, 17, 5843–5845 and refs. therein.
(18) Inanaga, K.; Takasu, K.; Ihara, M. J. Am. Chem. Soc. 2005,
127, 3668–3669.
9
ACS Paragon Plus Environment