Please do not adjust margins
Chemical Science
Page 5 of 7
DOI: 10.1039/C8SC02279H
Journal Name
COMMUNICATION
and H. M. Nelson, Science, 2017, 355, 1403–1407; (h) H.
F. T. Klare, ACS Catal., 2017, , 6999–7002.
7
6
For recent examples, see: (a) D. J. Parks and W. E. Piers,
J. Am. Chem. Soc., 1996, 118, 9440–9441; (b) L. L. Adduci,
T. A. Bender, J. A. Dabrowski and M. R. Gagné, Nat.
Notes and references
§
In these reactions, the anion may also be serving as a
Lewis base activator for the allyltrimethylsilane. In
support of this idea, we found that TMSOTf did not
catalyze this reaction. Thus, we speculate that the
cyclopentadienyl anions provide sufficient Lewis acid and
Lewis base character for activation of both electrophile
and nucleophile in this process.
Chem., 2015, 7, 576–581; (c) M. Oestreich, J. Hermeke
and J. Mohr, Chem. Soc. Rev., 2015, 44, 2202–2220; (d) B.
S. Moyer and M. R. Gagné, Synlett, 2017, 28, 2429–2434;
(e) A. Gudz, P. R. Payne and M. R. Gagné,
Organometallics, 2017, 36, 4047–4053; (f) T. A. Bender,
P. R. Payne and M. R. Gagné, Nat. Chem., 2018, 10, 85–
90.
1
2
(a) J. B. Lambert, L. Kania and S. Zhang, Chem. Rev., 1995,
95, 1191–1201; (b) J. Belzner, Angew. Chem. Int. Ed. Eng.,
1997, 36, 1277–1280; (c) C. A. Reed, Acc. Chem. Res.,
1998, 31, 325–332; (d) J. B. Lambert, Y. Zhao and S. M.
Zhang, J. Phys. Org. Chem., 2001, 14, 370–379; (e) K.-C.
Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin
and J. B. Lambert, Science, 2002, 297, 825–827.
7
8
S. M. Banik, A. Levina, A. M. Hyde and E. N. Jacobsen,
Science, 2017, 358, 761–764.
(a) C. D. Gheewala, B. E. Collins and T. H. Lambert,
Science, 2016, 351, 961–965; (b) C. D. Gheewala, M. A.
Radtke, J. Hui, A. B. Hon and T. H. Lambert, Org. Lett.,
2017, 19, 4227–4230; (c) C. D. Gheewala, J. S. Hirschi,
W.-H. Lee, D. W. Paley, M. J. Vetticatt and T. H. Lambert,
J. Am. Chem. Soc., 2018, 140, 3523–3527.
For representative examples, see: (a) M. Johannsen, K. A.
Jørgensen and G. Helmchen, J. Am. Chem. Soc., 1998,
120, 7637–7638; (b) G. A. Olah, G. Rasul and G. K. S.
Prakash, J. Am. Chem. Soc., 1999, 121, 9615–9617; (c) B.
Mathieu, L. de Fays and L. Ghosez, Tetrahedron Lett.,
2000, 41, 9561–9564; (d) T. Hoshi, H. Shionoiri, M.
Katano, T. Suzuki and H. Hagiwara, Tetrahedron:
Asymmetry, 2002, 13, 2167–2175; (e) K. Kubota, C. L.
Hamblett, X. Wang and J. L. Leighton, Tetrahedron, 2006,
62, 11397–11401; (f) Z. Tang, B. Mathieu, B. Tinant, G.
Dive and L. Ghosez, Tetrahedron, 2007, 63, 8449–8462;
(g) G. T. Notte and J. L. Leighton, J. Am. Chem. Soc., 2008,
130, 6676–6677; (h) H. F. T. Klare and M. Oestreich, Dalt.
Trans., 2010, 39, 9176–9184; (i) A. Schulz and A. Villinger,
Angew. Chem. Int. Ed., 2012, 51, 4526–4528; (j) Y.
Sakaguchi, Y. Iwade, T. Sekikawa, T. Minami and Y.
Hatanaka, Chem. Commun., 2013, 49, 11173–11175; (k)
T. Müller, in Structure and Bonding, ed. D.
Scheschkewitz, Springer, Berlin, 2014, pp. 107–162; (l) V.
H. G. Rohde, M. F. Müller and M. Oestreich,
Organometallics, 2015, 34, 3358–3373; (m) R. Maskey,
M. Schädler, C. Legler and L. Greb, Angew. Chem. Int. Ed.,
2018, 57, 1717–1720.
9
R. Vianello and Z. B. Maksić, Tetrahedron, 2005, 61
9381–9390.
,
10
11
C. Richardson and C. A. Reed, Chem. Commun., 2004, 5
706–707.
,
(a) T. Sakai, S. Seo, J. Matsuoka and Y. Mori, J. Org.
Chem., 2013, 78, 10978–10985; (b) T. Sakai, J. Matsuoka,
M. Shintai and Y. Mori, J. Org. Chem., 2017, 82, 3276-
3283.
12
13
K. Kubota and J. L. Leighton, Angew. Chem. Int. Ed., 2003,
42, 946–948.
For examples of halide abstraction, see: (a) R. Panisch,
M. Bolte and T. Müller, J. Am. Chem. Soc., 2006, 128
,
9676–9682; (b) R. Hayashi and G. R. Cook, Tetrahedron
Lett., 2008, 49, 3888–3890; (c) C. B. Caputo and D. W.
Stephan, Organometallics, 2012, 31
Ahrens, G. Scholz, T. Braun and E. Kemnitz. Angew.
Chem. Int. Ed., 2013, 52 5328-5332; (e) P. A.
, 27–30; (d) M.
,
Champagne, Y. Benhassine, J. Desroches and J. F. Paquin,
Angew. Chem. Int. Ed., 2014, 53, 13835–13839; (f) P. A.
Champagne, M. Drouin, C. Y. Legault, C. Audubert and J.
F. Paquin, J. Fluor. Chem., 2015, 171, 113–119; (g) R.
Hemelaere, P. A. Champagne, J. Desroches and J. F.
Paquin, J. Fluor. Chem., 2016, 190, 1–6; (h) S. Yoshida, K.
Shimomori, Y. Kim and T. Hosoya, Angew. Chem. Int. Ed.,
2016, 55, 10406–10409; (i) T. Kumar, F. Massicot, D.
Harakat, S. Chevreux, A. Martinez, K. Bordolinska, P.
Preethalayam, R. Kokkuvayil Vasu, J. B. Behr, J. L. Vasse
and F. Jaroschik, Chem. Eur. J., 2017, 23, 16460–16465;
(j) J. D. Hamel, M. Beaudoin, M. Cloutier and J. F. Paquin,
Synlett, 2017, 28, 2823–2828; (k) K. Saito, T. Umi, T.
Yamada, T. Suga and T. Akiyama, Org. Biomol. Chem.,
2017, 15, 1767–1770; (l) I. Mallov, A. J. Ruddy, H. Zhu, S.
3
4
I. Krossing and I. Raabe, Angew. Chem. Int. Ed., 2004, 43,
2066–2090.
(a) T. Gatzenmeier, M. van Gemmeren, Y. Xie, D. Höfler,
M. Leutzsch and B. List, Science, 2016, 351, 949–952; (b)
Z. Zhang, H. Y. Bae, J. Guin, C. Rabalakos, M. van
Gemmeren, M. Leutzsch, M. Klussmann and B. List, Nat.
Commun., 2016, 7, 12478–12485; (c) P. Pommerening, J.
Mohr, J. Friebel and M. Oestreich, Eur. J. Org. Chem.,
2017, 2017, 2312–2316; (d) C. K. De, R. Mitra and B. List,
Synlett, 2017, 28, 2435–2438.
5
For example: (a) Z. Xie, J. Manning, R. W. Reed, R.
Mathur, P. D. W. Boyd, A. Benesi and C. A. Reed, J. Am.
Chem. Soc., 1996, 118, 2922–2928; (b) C. Douvris and O.
Grimme and D. W. Stephan, Chem. Eur. J., 2017, 23
17692–17696.
,
V. Ozerov, Science, 2008, 321, 1188–1190; (c) S.
Duttwyler, C. Douvris, N. L. P. Fackler, F. S. Tham, C. A.
Reed, K. K. Baldridge and J. S. Siegel, Angew. Chem. Int.
Ed., 2010, 49, 7519–7522; (d) C. A. Reed, Acc. Chem. Res.,
2010, 43, 121–128; (e) C. Douvris, C. M. Nagaraja, C.-H.
Chen, B. M. Foxman and O. V. Ozerov, J. Am. Chem. Soc.,
2010, 132, 4946–4953; (f) O. Allemann, S. Duttwyler, P.
Romanato, K. K. Baldridge and J. S. Siegel, Science, 2011,
332, 574–577; (g) B. Shao, A. L. Bagdasarian, S. Popov
14
For examples of allylations achieved via this strategy: (a)
T. Saito, Y. Nishimoto, M. Yasuda and A. Baba, J. Org.
Chem., 2007, 72, 8588–8590; (b) M. Barbero, S. Bazzi, S.
Cadamuro, S. Dughera and C. Piccinini, Synthesis
(Stuttg)., 2010, 315–319; (c) H. T. Dao, U. Schneider and
S. Kobayashi, Chem. Commun., 2011, 47, 692–694; (d) L.
Y. Chan, S. Kim, W. T. Chung, C. Long and S. Kim, Synlett,
2011,
2, 415–419; (e) J. Zhu, M. Pérez and D. W. Stephan,
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins