Journal of the American Chemical Society
Article
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(4) Examples of copper(I)-catalyzed borylative aldol reactions:
(a) Chen, I. H.; Yin, L.; Itano, W.; Kanai, M.; Shibasaki, M. J. Am.
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(5) For examples of copper(I)-mediated carboboration of alkynes:
(a) Okuno, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2011,
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(6) Kehr, G.; Erker, G. Chem. Commun. 2012, 48, 1839.
(7) For copper(I)-catalyzed endo-cyclizations: (a) Ito, H.; Kosaka, Y.;
Nonoyama, K.; Sasaki, Y.; Sawamura, M. Angew. Chem., Int. Ed. 2008,
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(8) For a review including copper(I)-catalyzed borylation: (a) Dang,
L.; Lin, Z. Y.; Marder, T. B. Chem. Commun. 2009, 3987. (b) Cid, J.;
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Gulyas, H.; Carbo, J. J.; Fernandez, E. Chem. Soc. Rev. 2012, 41, 3558.
(9) For copper(I)-catalyzed boryl substitution of alkyl halides:
(a) Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang, J.; Liu,
J.-H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew.
Chem., Int. Ed. 2012, 51, 528. Soon after this publication, a similar
reaction was reported: (b) Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890.
For related copper(I)-catalyzed boryl substitution of aryl halides:
(c) Kleeberg, C.; Dang, L.; Lin, Z. Y.; Marder, T. B. Angew. Chem., Int.
Ed. 2009, 48, 5350.
(10) One example of copper(I)-catalyzed reaction that gave the same
cyclization product was reported in ref 9a. Details are discussed in this
Article.
(11) Examples of the copper(I)-catalyzed borylation of activated
alkenes: (a) Ito, H.; Yamanaka, H.; Tateiwa, J.; Hosomi, A.
Tetrahedron Lett. 2000, 41, 6821. (b) Takahashi, K.; Ishiyama, T.;
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(13) Diborations of unactivated alkenes were reported. For examples
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Int. Ed. 2008, 47, 5194. For examples of organocatalysis: (e) Bonet,
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2005, 3056. (e) Ramírez, J.; Sanau, M.; Fernan
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(14) Reaction of a tertiary alkenyl bromide, 1-allyl-1-bromocyclohex-
ane, gave the corresponding borylative cyclization product in low yield
1
(38%, determined by H NMR).
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(19) Bernstein, P.; Brown, D.; Griffin, A.; Tremblay, M. C.;
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dx.doi.org/10.1021/ja3104582 | J. Am. Chem. Soc. 2013, 135, 2635−2640