10.1002/anie.201811782
Angewandte Chemie International Edition
COMMUNICATION
In summary, we have described a catalytic vinylidenation of
organoboronic esters that provides a new synthesis route to
alkenylboronic esters.
This work was supported by the NIH (GM-R35-127140).
Keywords: • Boron • Allyl Complex • Palladium • Catalysis
Acknowledgements
(1) D. G. Hall, Ed. Boronic Acids: Preparation, Applications in Organic Synthesis
and Medicine, 2nd ed.; Wiley-VCH: Weinheim, 2011.
(11) J. Takagi, K. Takahashi, T. Ishiyama, N. Miyaura J. Am. Chem. Soc. 2002,
124, 8001.
(2) H. C. Brown, C. Synder, B. C. Subba Rao, G. Zweifel Tetrahedron 1986, 42,
5505.
(12) W. Guan, A. K. Michael, M. L. McIntosh, L. Koren-Selfridge, J. P. Scott, T.
B. Clark J. Org. Chem. 2014, 79, 7199.
(3) S. N. Mlynarski, A. S. Karns, J. P. Morken J. Am. Chem. Soc. 2012, 134,
16449.
(13) J. R. Coombs, L. Zhang, J. P. Morken Org. Lett. 2015, 17, 1708.
(14) E. M. Woerly, J. E. Miller, M. D. Burke Tetrahedron 2013, 69, 7732.
(15) L. Zhang, G. J. Lovinger, E. K. Edelstein, A. A. Szymaniak, M. P. Chierchia,
J. P. Morken Science 2016, 351, 6268.
(4) (a) N. Miyaura, A. Suzuki Chem. Rev. 1995, 95, 2457. (b) A. J. Lennox, G.
C. Lloyd-Jones Chem. Soc. Rev. 2014, 43, 412. (c) A. H. Cherney, N. T.
Kadunce, S. E. Reisman Chem. Rev. 2015, 115, 9587. (d) J. P. G. Rygus,
C. M. Crudden J. Am. Chem. Soc. 2017, 139, 18124.
(16) G. J. Lovinger, M. D. Aparece, J. P. Morken J. Am. Chem. Soc. 2017, 139,
3153.
(5) D. S. Matteson, K. M. Sadhu J. Am. Chem. Soc. 1983, 105, 2077.
(6) Y. Wang, A. Noble, E. L. Myers, V. K. Aggarwal Angew. Chem. Int. Ed. 2016,
55, 4270.
(17) E. K. Edelstein, S. Namirembe, J. P. Morken J. Am. Chem. Soc. 2017, 139,
5027.
(18) M. P. Chierchia, C. Law, J. P. Morken Angew. Chem. Int. End. 2017, 56,
11870.
(7) (a) G. Zweifel, N. L. Polston, C. C. Whitney J. Am. Chem. Soc. 1963, 90,
6243. (b) D. S. Matteson Synthesis 1975, 147. (c) D. S. Matteson, P. K.
Jesthi J. Organomet. Chem. 1976, 110, 25. (d) D. A. Evans, R. C.
Thomas, J. A. Walker Tetrahedron Lett. 1976, 17, 1427. (e) D. A. Evans,
T. C. Crawford, R. C. Thomas, J. A. Walker J. Org. Chem. 1976, 41,
3947. For a recent advance in this area, see: (f) R. J. Armstrong, W.
Niwetmarin, V. K. Aggarwal Org. Lett. 2017, 19, 2762.
(19) G. J. Lovinger, J. P. Morken J. Am. Chem. Soc. 2017, 139, 17293.
(20) (a) S. Panda, J. M. Ready J. Am. Chem. Soc. 2017, 139, 6038. (b) S.
Panda, J. M. Ready J. Am. Chem. Soc. 2018, 140, 13242.
(21) (a) M. Ishikura, I. Agata Heterocycles 1996, 43, 1591. (b) M. Ishikura, H.
Kato Tetrahedron 2002, 58, 9827.
(22) N. Ishida, T. Shinmoto, S. Sawano, T. Miura, M. Murakami Bull. Chem.
Soc. Jpn. 2010, 83, 1380.
(8) R. J. Armstrong, C. García-Ruiz, E. L. Myers, V. K. Aggarwal Angew. Chem.,
Int. Ed. 2017, 56, 786.
(23) For seminal reports on β-hydride elimination reactions promoted by allyl
reagents as the oxidant, see: (a) I. Shimizu, J. Tsuji J. Am. Chem. Soc.
1982, 104, 5844. (b) I. Shimizu, I. Minami, J. Tsuji Tetrahedron Lett. 1983,
24, 1797. (c) I. Minami, K. Takahashi, I. Shimizu, T. Kimura, J. Tsuji
Tetrahedron 1986, 42, 2971. (d) Y. Shvo, Y., A. H. I. Arisha J. Org. Chem.
1998, 63, 5640.
(9) For a recent relevant b-hydrogen elimination with Pd(allyl) complexes,
see:(a) S. A. Murray, E. C. M. Luc, S. J. Meek Org. Lett. 2018, 20, 469.
(b) Y. Shvo, Y., A. H. I. Arisha J. Org. Chem. 1998, 63, 5640. (c) Y.
Chen, J. P. Romaire, T. R. Newhouse J. Am. Chem. Soc. 2015, 137,
5875. (d) Y. Chen, A. Turlik, T. R. Newhouse J. Am. Chem. Soc. 2016,
138, 1166. (e) Y. Chen, D. Huang, Y. Zhao, T. R. Newhouse Angew.
Chem. Int. Ed. 2017, 56, 8258. (f) D. Huang, Y. Zhao, T. R. Newhouse
Org. Lett. 2018, 20, 684.
(24) A. A. Szymaniak, C. Zhang, J. R. Coombs, J. P. Morken ACS Catal. 2018,
8, 2897.
(25) Y.-M. Chung, C. K. Wei, D.-W. Chuang, M. El-Shazly, C.-T. Hsieh, T. Asai,
Y. Oshima, T.-J. Hsieh, T.-L. Hwang, Y.-C. Wu, F.-R. Chang Bioorg. &
Med. Chem. 2013, 21, 3866.
(10) (a) F. Gao, A. H. Hoveyda J. Am. Chem. Soc. 2010, 132, 10961. (b) H.
Jang, A. R. Zhugralin, Y. Lee, A. H. Hoveyda J. Am. Chem. Soc. 2011,
133, 7859. (c) A. L. Moure, R. G. Arrayás, D. J. Cárdenas, I. Alonso, J.
C. Carretero J. Am. Chem. Soc. 2012, 134, 7219. (d) A. L. Moure, P.
Mauleón, R. G. Arrayás, J. C. Carretero Org. Lett. 2013, 15, 2054. (e) A.
G. García-Rubia, J. A. Romero-Revilla, P. Mauleón, R. G. Arrayás, J. C.
Carretero J. Am. Chem. Soc. 2015, 137, 6857. (f) D. P. Ojha, K. R.
Prabhu Org. Lett. 2016, 18, 432. (g) H. Yoshida ACS Catal. 2016, 6,
1799.
(26) J. A. Myhill, L. Zhang, G. J. Lovinger, J. P. Morken Angew. Chem. Int. Ed.
2018, 57, 12799.
(27) For a recent review of agostic interactions, see: M. Brookhart, M. L. H.
Green, G. Parkin Proc. Nat. Acad. Sci. 2007, 104, 6908.
This article is protected by copyright. All rights reserved.