10.1002/anie.201805476
Angewandte Chemie International Edition
COMMUNICATION
A. H. Hoveyda, Angew. Chem. Int. Ed. 2016, 55, 3455; Angew. Chem.
2016, 128, 3516; g) M. Zhan, R.-Z. Li, Z.-D. Mou, C.-G. Cao, J. Liu, Y.-
W. Chen, D. Niu, ACS Catal. 2016, 6, 3381; h) J. Kim, K. Ko, S. H. Cho,
Angew. Chem. Int. Ed. 2017, 56, 11584; Angew. Chem. 2017, 129,
11742; i) T. Miura, J. Nakahashi, M. Murakami, Angew. Chem. Int. Ed.
2017, 56, 6989; Angew. Chem. 2017, 129, 7093; j) T. Miura, J.
Nakahashi, W. Zhou, Y. Shiratori, S. G. Stewart, M. Murakami, J. Am.
Chem. Soc. 2017, 139, 10903;
[18] For a recent review, see: a) J. Qu, G. Helmchen, Acc. Chem. Res. 2017,
50, 2539 and references cited therein. For recent selected examples,
see: b) S. L. Rössler, S. Krautwald, E. M. Carreira, J. Am. Chem. Soc.
2017, 139, 3603; c) J. Y. Hamilton, S. L. Rössler, E. M. Carreira, J. Am.
Chem. Soc. 2017, 139, 8082; d) T. Sandmeier, S. Krautwald, E. M.
Carreira, Angew. Chem. Int. Ed. 2017, 56, 11515; Angew. Chem. 2017,
129, 11673; e) M. A. Schafroth, S. M. Rummelt, D. Sarlah, E. M. Carreira,
Org. Lett. 2017, 19, 3235.
[6]
a) K. Hong, X. Liu, J. P. Morken, J. Am. Chem. Soc. 2014, 136, 10581;
b) J. R. Coombs, L. Zhang, J. P. Morken, J. Am. Chem. Soc. 2014, 136,
16140. c) W. Jo, J. Kim, S. Choi, S. H. Cho, Angew. Chem. Int. Ed. 2016,
55, 9690; Angew. Chem. 2016, 128, 9842; d) J. Kim, S. H. Cho, Synlett
2016, 27, 2525; e) D. J. Blair, D. Tanini, J. M. Bateman, H. K. Scott, E.
L. Myers, V. K. Aggarwal, Chem. Sci. 2017, 8, 2898; f) C. Hwang, W. Jo,
S. H. Cho, Chem. Commun. 2017, 53, 7573; g) Y. Lee, S.-y. Baek, J.
Park, S.-T. Kim, S. Tussupbayev, J. Kim, M.-H. Baik, S. H. Cho, J. Am.
Chem. Soc. 2017, 139, 976; h) J. Park, S. Choi, Y. Lee, S. H. Cho, Org.
Lett. 2017, 19, 4054; i) Y. Ayaka, N. Kazunori, I. Tomohiro, O. Hirohisa,
S. Masaya, Angew. Chem. Int. Ed. 2018, 57, 3196; Angew. Chem. 2018,
130, 3250; j) W. Sun, L. Wang, X. Xia, C. Liu, Angew. Chem. Int. Ed.
2018, 57, 5501; Angew. Chem. 2018, 130, 5599.
[19] We assumed that the coordination of zinc to one of oxygens of Bpin
group might have an effect to stabilize (diborylmethyl)zinc species. For
details, see: a) D. S. Matteson, E. Erdik, Organometallics 1983, 2, 1083;
b) D. S. Matteson, K. M. Sadhu, J. Am. Chem. Soc. 1983, 105, 2077; c)
D. S. Matteson, K. M. Sadhu, Organometallics 1984, 3, 614; d) D. S.
Matteson, K. M. Sadhu, J. Am. Chem. Soc. 1986, 108, 810; e) M. M.
Midland, J. Org. Chem. 1998, 63, 914; f) D. S. Matteson, J. Org. Chem.
2013, 78, 10009. Further experimental and computational studies are
ongoing to elucidate the structure of (diborylmethyl)zinc species.
[20] a) F. Dübner, P. Knochel, Angew. Chem. Int. Ed. 1999, 38, 379; Angew.
Chem. 1999, 111, 391; b) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy,
A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456; Angew. Chem.
2001, 113, 1504; c) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa,
Org. Lett. 2001, 3, 1169; d) K. E. Murphy, A. H. Hoveyda, J. Am. Chem.
Soc. 2003, 125, 4690; e) U. Piarulli, P. Daubos, C. Claverie, M. Roux, C.
Gennari, Angew. Chem. Int. Ed. 2003, 42, 234; Angew. Chem. 2003, 115,
244; f) A. O. Larsen, W. Leu, C. N. Oberhuber, J. E. Campbell, A. H.
Hoveyda, J. Am. Chem. Soc. 2004, 126, 11130; g) A. W. van Zijl, L. A.
Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413;
h) P. J. Goldsmith, S. J. Teat, S. Woodward, Angew. Chem. Int. Ed. 2005,
44, 2235; Angew. Chem. 2005, 117, 2275; i) N. Yoshikai, K. Miura, E.
Nakamura, Adv. Synth. Catal. 2009, 351, 1014; j) A. Misale, S.
Niyomchon, M. Luparia, N. Maulide, Angew. Chem. Int. Ed. 2014, 53,
7068; Angew. Chem. 2014, 126, 7188; k) J. H. Kim, Y. O. Ko, J. Bouffard,
S.-g. Lee, Chem. Soc. Rev. 2015, 44, 2489.
[7]
a) D. S. Matteson, P. K. Jesthi, J. Organomet. Chem. 1976, 110, 25; b)
D. S. Matteson, R. J. Moody, J. Am. Chem. Soc. 1977, 99, 3196; c) D. S.
Matteson, R. J. Moody, Organometallics 1982, 1, 20.
[8]
[9]
a) J. R. Coombs, L. Zhang, J. P. Morken, Org. Lett. 2015, 17, 1708; b) T.
C. Stephens, G. Pattison, Org. Lett. 2017, 19, 3498.
a) S. A. Murray, M. Z. Liang, S. J. Meek, J. Am. Chem. Soc. 2017, 139,
14061; b) S. A. Murray, E. C. M. Luc, S. J. Meek, Org. Lett. 2018, 20,
469.
[10] C. E. Iacono, T. C. Stephens, T. S. Rajan, G. Pattison, J. Am. Chem. Soc.
2018, 140, 2036.
[11] a) Y. Miguel, O. Rosa, Eur. J. Org. Chem. 2004, 2004, 3833. b)
Rappoport, Z.; Marek, I. Eds., The Chemistry of Organozinc Compounds,
Wiley & Sons: Chichester, 2006; c) P. Knochel, R. D. Singer, Chem. Rev.
1993, 93, 2117; d) J. E. Fleckenstein, K. Koszinowski, Organometallics
2011, 30, 5018; e) S. H. Kyne, J. M. Percy, R. D. Pullin, J. M. Redmond,
P. G. Wilson, Org. Biomol. Chem. 2011, 9, 8328; f) C. J. Cordier, R. J.
Lundgren, G. C. Fu, J. Am. Chem. Soc 2013, 135, 10946; g) T. Klatt, J.
T. Markiewicz, C. Sämann, P. Knochel, J. Org. Chem. 2014, 79, 4253.
[12] For representative reviews, see: a) B. M. Trost, D. L. Van Vranken, Chem.
Rev. 1996, 96, 395; b) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103,
2921; c) L.-X. Dai, T. Tu, S.-L. You, W.-P. Deng, X.-L. Hou, Acc. Chem.
Res. 2003, 36, 659; d) Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47,
258; Angew. Chem. 2008, 120, 264;
[21] a) P. Damien, R. Xavier, F. C. A., L. Jean‐Baptiste, E. H. Samir, A.
Alexandre, Chem. Eur. J. 2009, 15, 1205; b) J. Y. Hamilton, D. Sarlah,
E. M. Carreira, Angew. Chem. Int. Ed. 2015, 54, 7644; Angew. Chem.
2015, 127, 7754.
[22] X.-J. Liu, S.-L. You, Angew. Chem. Int. Ed. 2017, 56, 4002; Angew.
Chem. 2017, 129, 4060.
[13] For selected reviews, see: a) A. Alexakis, J. E. Bäckvall, N. Krause, O.
Pàmies, M. Diéguez, Chem. Rev. 2008, 108, 2796; b) S. R. Harutyunyan,
T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa, Chem. Rev. 2008,
108, 2824; c) J.F.Teichert, B. L. Feringa, Angew.Chem. Int. Ed. 2010, 49,
2486; Angew.Chem. 2010, 122, 2538;
[14] For reviews of iridium-catalyzed allylic substitutions, see: a) H. Miyabe,
Y. Takemoto, Synlett 2005, 2005, 1641; b) R. Takeuchi, S. Kezuka,
Synthesis 2006, 2006, 3349; c) G. Helmchen, A. Dahnz, P. Dubon, M.
Schelwies, R. Weihofen, Chem. Commun. 2007, 675; d) J. F. Hartwig, L.
M. Stanley, Acc. Chem. Res. 2010, 43, 1461; e) J. F. Hartwig, M. J. Pouy,
in Top. Organomet. Chem. 2011, 34, 169; f) W.-B. Liu, J.-B. Xia, S.-L.
You, in Top. Organomet. Chem. 2012, 38, 155; g) P. Tosatti, A. Nelson,
S. P. Marsden, Org. Biomol. Chem. 2012, 10, 3147; h) J. C. Hethcox, S.
E. Shockley, B. M. Stoltz, ACS Catal. 2016, 6, 6207.
[15] a) R. Takeuchi, N. Ue, K. Tanabe, K. Yamashita, N. Shiga, J. Am. Chem.
Soc 2001, 123, 9525; b) T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc.
2002, 124, 15164; c) M. Lafrance, M. Roggen, E. M. Carreira, Angew.
Chem. Int. Ed. 2012, 51, 3470; Angew. Chem. 2012, 124, 3527; d) W. K.
Walker, D. L. Anderson, R. W. Stokes, S. J. Smith, D. J. Michaelis, Org.
Lett. 2015, 17, 752; e) X. Zhang, W.-B. Liu, Q. Cheng, S.-L. You,
Organometallics 2016, 35, 2467.
[16] The purity of 2a was determined by titration using diphenylacetic acid as
a titrant. For details, see the Supporting Information.
[17] See the Supporting Information for details.
This article is protected by copyright. All rights reserved.