Organic Letters
Letter
M.; et al. 6-Arylalkylamino- 2,3,4,5-Tetrahydro-1H-Benzo[d]Azepines
as 5-Ht2c Receptor Agonists. WO2007028083 (A2), March 8, 2007.
ACKNOWLEDGMENTS
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This work is supported by the Swiss National Science
Foundation.
REFERENCES
■
(1) Williams, J. M. J. Preparation of Alkenes: A Practical Approach;
Oxford University Press, 1996.
(2) Siau, W.-Y.; Zhang, Y.; Zhao, Y. Stereoselective Synthesis of Z-
Alkenes. Top. Curr. Chem. 2012, 327, 33−58.
(3) Hall, D. G. Structure, Properties, and Preparation of Boronic
Acid Derivatives. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH
(4) Rawat, V. S.; Sreedhar, B. Iron-Catalyzed Borylation Reactions of
Alkynes: An Efficient Synthesis of E-Vinyl Boronates. Synlett 2014, 25
(08), 1132−1136.
(5) PraveenGanesh, N.; d’Hond, S.; Chavant, P. Y. Methylpentane-
diolborane: Easy Access to New Air- and Chromatography-Stable,
Highly Functionalized Vinylboronates. J. Org. Chem. 2007, 72 (12),
4510−4514.
(6) Ho, H. E.; Asao, N.; Yamamoto, Y.; Jin, T. Carboxylic Acid-
Catalyzed Highly Efficient and Selective Hydroboration of Alkynes
with Pinacolborane. Org. Lett. 2014, 16 (17), 4670−4673.
(7) Tucker, C. E.; Davidson, J.; Knochel, P. Mild and Stereoselective
Hydroborations of Functionalized Alkynes and Alkenes Using
Pinacolborane. J. Org. Chem. 1992, 57 (12), 3482−3485.
(8) Pereira, S.; Srebnik, M. A Study of Hydroboration of Alkenes
and Alkynes with Pinacolborane Catalyzed by Transition Metals.
Tetrahedron Lett. 1996, 37 (19), 3283−3286.
(9) Shirakawa, K.; Arase, A.; Hoshi, M. Preparation of (E)-1-
Alkenylboronic Acid Pinacol Esters via Transfer of Alkenyl Group
from Boron to Boron. Synthesis 2004, 2004 (11), 1814−1820.
(10) Ben-Daat, H.; Rock, C. L.; Flores, M.; Groy, T. L.; Bowman, A.
C.; Trovitch, R. J. Hydroboration of Alkynes and Nitriles Using an α-
Diimine Cobalt Hydride Catalyst. Chem. Commun. 2017, 53 (53),
7333−7336.
(11) Obligacion, J. V.; Chirik, P. J. Earth-Abundant Transition Metal
Catalysts for Alkene Hydrosilylation and Hydroboration. Nature
Reviews Chemistry 2018, 2 (5), 15.
̈
(12) Gunanathan, C.; Holscher, M.; Pan, F.; Leitner, W. Ruthenium
Catalyzed Hydroboration of Terminal Alkynes to Z-Vinylboronates. J.
Am. Chem. Soc. 2012, 134 (35), 14349−14352.
(13) Ohmura, T.; Yamamoto, Y.; Miyaura, N. Rhodium- or Iridium-
Catalyzed Trans-Hydroboration of Terminal Alkynes, Giving (Z)-1-
Alkenylboron Compounds. J. Am. Chem. Soc. 2000, 122 (20), 4990−
4991.
̈
(14) Gorgas, N.; Alves, L. G.; Stoger, B.; Martins, A. M.; Veiros, L.
F.; Kirchner, K. Stable, Yet Highly Reactive Nonclassical Iron(II)
Polyhydride Pincer Complexes: Z-Selective Dimerization and Hydro-
boration of Terminal Alkynes. J. Am. Chem. Soc. 2017, 139 (24),
8130−8133.
(15) Obligacion, J. V.; Neely, J. M.; Yazdani, A. N.; Pappas, I.;
Chirik, P. J. Cobalt Catalyzed Z-Selective Hydroboration of Terminal
Alkynes and Elucidation of the Origin of Selectivity. J. Am. Chem. Soc.
2015, 137 (18), 5855−5858.
(16) Cheung, C. W.; Zhurkin, F. E.; Hu, X. Z-Selective Olefin
Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides
with Terminal Arylalkynes. J. Am. Chem. Soc. 2015, 137 (15), 4932−
4935.
(17) Cheung, C. W.; Hu, X. Stereoselective Synthesis of
Trisubstituted Alkenes through Sequential Iron-Catalyzed Reductive
Anti-Carbozincation of Terminal Alkynes and Base-Metal-Catalyzed
Negishi Cross-Coupling. Chem. - Eur. J. 2015, 21 (50), 18439−18444.
(18) Zhurkin, F. E.; Hu, X. γ-Selective Allylation of (E)-Alkenylzinc
Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl
Iodides. J. Org. Chem. 2016, 81 (13), 5795−5802.
(19) Briner, K.; Adeva, B.; Cases-Thomas, M.; Galka, C.; Marcos, L.;
Martinez-Grau, M.; Mazanetz, M.; O’toole, J.; Rathmell, R.; Reinhard,
D
Org. Lett. XXXX, XXX, XXX−XXX