Organic Letters
Letter
Frejd, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 376−377. (c) Giffels,
G.; Dreisbach, C.; Kragl, U.; Weigerding, M.; Waldmann, H.;
Wandrey, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2005−2006.
(8) Bagherzadeh, S.; Mankad, N. P. Chem. Commun. 2016, 52, 3844−
3846.
Scheme 2. Proposed Mechanism for Hydroboration of
Carbonyl Compounds Catalyzed by Aluminum
Monohydride Complex (1)
(9) (a) Lummis, P. A.; Momeni, M. R.; Lui, M. W.; McDonald, R.;
Ferguson, M. J.; Miskolzie, M.; Brown, A.; Rivard, E. Angew. Chem., Int.
Ed. 2014, 53, 9347−9351. (b) Roh, S. G.; Yoon, J. U.; Jeong, J. H.
Polyhedron 2004, 23, 2063−2067. (c) Locatelli, M.; Cozzi, P. G.
Angew. Chem., Int. Ed. 2003, 42, 4928−4930. (d) Bandini, M.; Cozzi,
P. G.; De Angelis, M.; Umani-Ronchi, A. Tetrahedron Lett. 2000, 41,
1601−1605.
(10) For a review on hydroboration of carbonyl compounds, see:
Chong, C. C.; Kinjo, R. ACS Catal. 2015, 5, 3238−3259.
(11) (a) Fohlmeister, L.; Stasch, A. Chem. - Eur. J. 2016, 22, 10235−
10246. (b) Chong, C. C.; Hirao, H.; Kinjo, R. Angew. Chem., Int. Ed.
2015, 54, 190−194. (c) Hadlington, T. J.; Hermann, M.; Frenking, G.;
Jones, C. J. Am. Chem. Soc. 2014, 136, 3028−3031. (d) Arrowsmith,
M.; Hadlington, T. J.; Hill, M. S.; Kociok-Koehn, G. Chem. Commun.
2012, 48, 4567−4569. (e) Blake, A. J.; Cunningham, A.; Ford, A.;
Teat, S. J.; Woodward, S. Chem. - Eur. J. 2000, 6, 3586−3594.
(12) Selected reviews: (a) Mandal, S. K.; Roesky, H. W. Acc. Chem.
Res. 2012, 45, 298−307. (b) Martin, D.; Soleilhavoup, M.; Bertrand, G.
Chem. Sci. 2011, 2, 389−399. (c) Yao, S.-L.; Xiong, Y.; Driess, M.
Organometallics 2011, 30, 1748−1767. (d) Asay, M.; Jones, C.; Driess,
M. Chem. Rev. 2011, 111, 354−396. (e) Stephan, D. W.; Erker, G.
Angew. Chem., Int. Ed. 2010, 49, 46−76. (f) Power, P. P. Nature 2010,
463, 171−177.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures and characterization data
Crystallographic data for the new compounds (CIF,
(13) (a) Liu, X.; Langmi, H. W.; Beattie, S. D.; Azenwi, F. F.;
McGrady, G. S.; Jensen, C. M. J. Am. Chem. Soc. 2011, 133, 15593−
15597. (b) Aldridge, S.; Downs, A. J. Chem. Rev. 2001, 101, 3305−
3366.
(14) Selected references: (a) Franz, D.; Inoue, S. Chem. - Eur. J. 2014,
20, 10645−10649. (b) Tan, G.; Szilvasi, T.; Inoue, S.; Blom, B.; Driess,
́
AUTHOR INFORMATION
Corresponding Author
■
M. J. Am. Chem. Soc. 2014, 136, 9732−9742. (c) Abdalla, J. A. B.;
Riddlestone, I. M.; Turner, J.; Kaufman, P. A.; Tirfoin, R.; Phillips, N.;
Aldridge, S. Chem. - Eur. J. 2014, 20, 17624−17634. (d) Fettinger, J.
C.; Gray, P. A.; Melton, C. E.; Power, P. P. Organometallics 2014, 33,
6232−6240. (e) Myers, T. W.; Berben, L. A. J. Am. Chem. Soc. 2013,
135, 9988−9990. (f) Riddlestone, I. M.; Edmonds, S.; Kaufman, P. A.;
Urbano, J.; Bates, J. I.; Kelly, M. J.; Thompson, A. L.; Taylor, R.;
Aldridge, S. J. Am. Chem. Soc. 2012, 134, 2551−2554. (g) Harder, S.;
Spielmann, J. Chem. Commun. 2011, 47, 11945−11947. (h) Bonyhady,
S. J.; Collis, D.; Frenking, G.; Holzmann, N.; Jones, C.; Stasch, A. Nat.
Author Contributions
†V.K.J. and M.K.B. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The authors thank the National Institute of Science Education
and Research (NISER), Bhubaneswar, Department of Atomic
Energy (DAE), Govt. of India and Science and Engineering
Research Board (SERB), Department of Science and
Technology (DST) for the research grant No. SR/S1/IC-52/
2012.
́
Chem. 2010, 2, 865−869. (i) Gonzalez-Gallardo, S.; Jancik, V.; Cea-
Olivares, R.; Toscano, R. A.; Moya-Cabrera, M. Angew. Chem., Int. Ed.
2007, 46, 2895−2898. (j) Cole, M. L.; Jones, C.; Junk, P. C.; Kloth,
M.; Stasch, A. Chem. - Eur. J. 2005, 11, 4482−4491. (k) Cui, C.;
Roesky, H. W.; Hao, H.; Schmidt, H.-G.; Noltemeyer, M. Angew.
Chem., Int. Ed. 2000, 39, 1815−1817.
(15) Bhadbhade, M.; Clentsmith, G. K. B.; Field, L. D. Organo-
metallics 2010, 29, 6509−6517.
(16) CCDC-1494396 (1).
(17) Chu, T.; Korobkov, I.; Nikonov, G. I. J. Am. Chem. Soc. 2014,
136, 9195−9202.
(18) Yang, Z.; Zhong, M.; Ma, X.; De, S.; Anusha, C.; Parameswaran,
P.; Roesky, H. W. Angew. Chem., Int. Ed. 2015, 54, 10225−10229.
(19) CCDC-1494397 (2m).
REFERENCES
■
(1) Chakraborty, S.; Bhattacharya, P.; Dai, H.; Guan, H. Acc. Chem.
Res. 2015, 48, 1995−2003. (b) Magano, J.; Dunetz, J. R. Org. Process
Res. Dev. 2012, 16, 1156−1184. (c) Cho, B. T. Chem. Soc. Rev. 2009,
38, 443−452.
(2) (a) Ito, J.-i.; Nishiyama, H. Tetrahedron Lett. 2014, 55, 3133−
3146. (b) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97−102.
(3) Korshin, E. E.; Leitus, G. M.; Bendikov, M. Org. Biomol. Chem.
2014, 12, 6661−6671.
(4) Evans, D. A.; Fu, G. C. J. Org. Chem. 1990, 55, 5678−5680.
(5) (a) Kaithal, A.; Chatterjee, B.; Gunanathan, C. Org. Lett. 2015,
17, 4790−4793. (b) Koren-Selfridge, L.; Londino, H. N.; Vellucci, J.
K.; Simmons, B. J.; Casey, C. P.; Clark, T. B. Organometallics 2009, 28,
2085−2090.
(6) Khalimon, A. Y.; Farha, P.; Kuzmina, L. G.; Nikonov, G. I. Chem.
Commun. 2012, 48, 455−457.
(7) (a) Oluyadi, A. A.; Ma, S.; Muhoro, C. N. Organometallics 2013,
32, 70−78. (b) Almqvist, F.; Torstensson, L.; Gudmundsson, A.;
D
Org. Lett. XXXX, XXX, XXX−XXX