Organic Letters
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006, 45, 3635−3638. (c) Ricardo, M. G.; Llanes, D.; Wessjohann, L.
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AUTHOR INFORMATION
(
9) (a) Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P.
■
*
M. P. Boronic Acids and Esters in the Petasis-Borono Mannich
Multicomponent Reaction. Chem. Rev. 2010, 110, 6169−6193.
b) Batey, R. A. Nucleophilic Addition Reactions of Aryl and
(
ORCID
Alkenylboronic Acids and Their Derivatives to Imines and Iminium
Ions. In Boronic Acids: Preparation and Applications in Organic
Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim,
Germany, 2005; pp 279−304. Some traceless examples: (c) Jiang, Y.;
Diagne, A. B.; Thomson, R. J.; Schaus, S. E. Enantioselective Synthesis
of Allenes by Catalytic Traceless Petasis Reactions. J. Am. Chem. Soc.
Author Contributions
§J.Y. and S.O.B. contributed equally to this work.
Notes
2
017, 139, 1998−2005. (d) Jiang, Y.; Thomson, R. J.; Schaus, S. E.
The authors declare no competing financial interest.
Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals:
Reductive Transposition of Allylic Diazenes. Angew. Chem., Int. Ed.
2
(
017, 56, 16631−16635.
ACKNOWLEDGMENTS
The authors are grateful for the generous financial support
provided by the NSF (CHE-1664818) and NIGMS (R01 GM
13878) to GM. J.Y. acknowledges funding from the National
■
10) (a) Miyaura, N.; Sasaki, N.; Itoh, M.; Suzuki, A. The coupling
reaction of copper(I) methyltrialkylborates with aroyl chlorides. A
convenient synthesis of alkyl aryl ketones from organoboranes.
Tetrahedron Lett. 1977, 18, 173−174. (b) Aggarwal, V. K.; Fang, G.
Y.; Ginesta, X.; Howells, D. M.; Zaja, M. Toward an understanding of
the factors responsible for the 1,2-migration of alkyl groups in borate
complexes. Pure Appl. Chem. 2006, 78, 215−229.
1
Natural Science Foundation of China (Grant No. 21602017),
the Natural Science Foundation of Jiangsu Province (Grant
No. BK20160405), the University Science Research Project of
Jiangsu Province (16KJB150001), and China Scholarship
Council (201708320115). R.A. thanks the Swedish Chemical
Society for a Bengt Lundqvist postdoctoral fellowship. We
thank Dr. Charles W. Ross III (UPenn) for his assistance in
obtaining HRMS data. Frontier Scientific is kindly acknowl-
edged for donating alkyl trifluoroborates in support of this
research. Kessil is acknowledged for providing the lights used
in this study.
(
11) (a) Hatano, M.; Suzuki, S.; Ishihara, K. Highly Efficient
Alkylation to Ketones and Aldimines with Grignard Reagents
Catalyzed by Zinc(II) Chloride. J. Am. Chem. Soc. 2006, 128,
9998−9999. (b) Hatano, M.; Yamashita, K.; Mizuno, M.; Ito, O.;
Ishihara, K. C-Selective and Diastereoselective Alkyl Addition to β,γ-
Alkynyl-α-imino Esters with Zinc(II)ate Complexes. Angew. Chem.,
Int. Ed. 2015, 54, 2707−2711.
(
12) (a) Plasko, D. P.; Jordan, C. J.; Ciesa, B. E.; Merrill, M. A.;
Hanna, J. M. Visible light-promoted alkylation of imines using
potassium organotrifluoroborates. Photochem. Photobiol. Sci. 2018, 17,
534−538. (b) Cao, K.; Tan, S. M.; Lee, R.; Yang, S.; Jia, H.; Zhao, X.;
Qiao, B.; Jiang, Z. Catalytic Enantioselective Addition of Prochiral
Radicals to Vinylpyridines. J. Am. Chem. Soc. 2019, 141, 5437−5443.
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