Journal of the American Chemical Society
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Experimental details for all reactions and for the sensitivity
assessment and characterization data for all products.
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AUTHOR INFORMATION
Boron–Carbon Bonds by Dichlorocarbene Insertion into the Boron–
Hydrogen Bond of Amine– and Phosphine–Boranes. Tetrahedron
2000, 56, 6039−6046. (f) Ramírez-Lꢆpez, P.; Sierra, M. A.; Gꢆmez-
Gallego, M.; Mancheꢇo, M. J.; Gornitzka, H. New Reactivity Modes of
Corresponding Author
Chromium(0) Fischer Carbene Complexes:ꢀ
Unprecedented
Notes
Insertion of a Carbene Ligand into an Active B−H Bond. Organomet.
2003, 22, 5092−5099. (g) Frey, G. D.; Masuda, J. D.; Donnadieu, B.;
Bertrand, G. Activation of Si−H, B−H, and P−H Bonds at a Single
Nonmetal Center. Angew. Chem., Int. Ed. 2010, 49, 9444−9447.
The authors declare no competing financial interests.
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ACKNOWLEDGMENT
(5) Li, X.; Curran, D. P. Insertion of Reactive Rhodium Carbenes
Generous financial support by the Alexander von Humboldt
Foundation (J.-H.Y.), the Alfried Krupp von Bohlen and Hal-
bach Foundation (L.Q., T.P.) and the Deutsche For-
schungsgemeinschaft (Leibniz Award) is gratefully acknowl-
edged. We thank Dr. Michael J. James, Felix Strieth-Kalthoff,
Dr. Zackaria Nairoukh, Dr. Tuhin Patra and Toryn Dalton for
helpful discussions.
into Boron−Hydrogen Bonds of Stable N‑Heterocyclic Carbene
Boranes. J. Am. Chem. Soc. 2013, 135, 12076−12081.
(6) Cheng, Q.-Q.; Zhu, S.-F.; Zhang, Y.-Z.; Xie, X.-L.; Zhou, Q.-L.
Copper-Catalyzed B−H Bond Insertion Reaction: A Highly Efficient
and Enantioselective C−B Bond-Forming Reaction with
Amine−Borane and Phosphine−Borane Adducts. J. Am. Chem. Soc.
2013, 135, 14094−14097.
(7) (a) Chen, D.; Zhang, X.; Qi, W.-Y.; Xu, B.; Xu, M.-H.
Rhodium(I)-Catalyzed Asymmetric Carbene Insertion into B−H
Bonds: Highly Enantioselective Access to Functionalized
Organoboranes. J. Am. Chem. Soc. 2015, 137, 5268−5271. (b) Cheng, Q.;
Xu, H.; Zhu, Shou.; Zhou, Q. Enantioselective Copper-Catalyzed B—
H Bond Insertion Reaction of α-Diazoketones. Acta Chim. Sinica
2015, 73, 326-329. (c) Hyde, S.; Veliks, J.; Liegault, B.; Grassi, D.;
Taillefer, M.; Gouverneur, V. Copper-Catalyzed Insertion into
Heteroatom–Hydrogen Bonds with Trifluorodiazoalkanes. Angew.
Chem., Int. Ed. 2016, 55, 3785−3789. (d) Allen, T. H.; Curran, D. P.
Relative Reactivity of Stable Ligated Boranes and a Borohydride Salt
in Rhodium(II)-Catalyzed Boron–Hydrogen Insertion Reactions. J.
Org. Chem. 2016, 81, 2094−2098. (e) Kan, S. B. J.; Huang, X.; Gumulya,
Y.; Chen, K.; Arnold, F.-H. Genetically Programmed Chiral
Organoborane Synthesis. Nature 2017, 552, 132−136. (f) Zeineddine, A.;
Rekhroukh, F.; Sosa Carrizo, E. D.; Mallet-Ladeira, S.; Miqueu, K.;
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