desired tertiary alcohols in considerably lower yields. Organo-
boronic esters bearing electron donating groups (and therefore
more nucleophilic) afford, in general, the desired tertiary
alcohols in higher yields and in shorter reaction times
(Table 2, entries 3–5, 6–8, 12–14), while the addition of
organoboronic esters bearing electron withdrawing groups
occurs in less extent (Table 2, entries 15–18).
5 Green Chemistry and Catalysis, ed. R. A. Sheldon, I. Arends and
U. Hanefeld, Wiley-VCH, Weiheim, 2007.
6 M. Hatano and K. Ishihara, Synthesis, 2008, 1647.
7 Boronic Acids, ed. D. G. Hall, Wiley-VCH, Weinheim, 2005.
8 (a) R. E. Mulvey, F. Mongin, M. Uchiyama and Y. Kondo,
Angew. Chem., Int. Ed., 2007, 46, 3802; (b) P. Knochel,
W. Dohle, N. Gommermann, F. F. Kniesel, F. Kopp, T. Knorn,
I. Sapountzis and V. A. Vu, Angew. Chem., Int. Ed., 2003, 42, 4302.
9 (a) W. Chen, M. Baghbanzadeh and C. O. Kappe, Tetrahedron
Lett., 2011, 52, 1677; (b) C. H. Xing and Q.-S. Hu, Tetrahedron
Lett., 2010, 51, 924; (c) J. Bouffard and K. Itami, Org. Lett., 2009,
11, 4410; (d) L. Zhou, X. Du, R. He, Z. Ci and M. Bao, Tetra-
hedron Lett., 2009, 50, 406; (e) F. Sakurai, K. Kondo and
T. Aoyama, Chem. Pharm. Bull., 2009, 57, 511;
(f) K. Yamamoto, K. Tsurumi, F. Sakurai, K. Kondo and
T. Aoyama, Synthesis, 2008, 3585; (g) T. Arao, K. Kondo and
T. Aoyama, Tetrahedron Lett., 2007, 48, 4115; (h) K. Hirano,
H. Yorimitsu and K. Oshima, Org. Lett., 2005, 7, 4689;
(i) G. Takahashi, E. Shirakawa, T. Tsuchimoto and
Y. Kawakami, Chem. Commun., 2005, 1459.
In summary, we have developed a Ni-catalysed domino
reaction that allows for the synthesis of tertiary alcohols from
secondary alcohols, in high yields and short reaction times.
Efforts on the expansion of this work to asymmetric systems
are currently ongoing in our laboratories.
This work was funded by the University of Hawaii. The
authors want to thank Walter Niemczura for his assistance
with the HRMS.
10 (a) Homogeneous Catalysis, ed. G. W. Parshall and S. Ittel, J. Wiley
and Sons, New York, 1983; (b) U. Christmann and R. Vilar,
Angew. Chem., Int. Ed., 2005, 44, 366; (c) M. W. Hooper,
M. Utsunomiya and J. F. Hartwig, J. Org. Chem., 2003, 68,
2861; (d) E. R. Strieter, D. G. Blackmond and S. L. Buchwald,
J. Am. Chem. Soc., 2003, 125, 13978.
Notes and references
1 C. Berini, D. F. Brayton, C. Mocka and O. Navarro, Org. Lett.,
2009, 11, 4244.
2 B. Landers, C. Berini, C. Wang and O. Navarro, J. Org. Chem.,
2011, 76, 1390.
3 C. Berini, O. H. Winkelmann, J. Otten, D. A. Vicic and
O. Navarro, Chem.–Eur. J., 2010, 16, 6857.
4 (a) Heterocyclic Carbenes in Transition Metals Catalysis
and Organocatalysis, ed. C. S. J. Cazin, Springer, London, 2010;
(b) N-Heterocyclic Carbenes in Transition Metal Catalysis,
ed. F. Glorius, Springer, Berlin, 2007.
11 (a) See, for instance: D. A. Wilson, C. J. Wilson, C. Moldoveanu,
A.-M. Resmerita, P. Corcoran, L. M. Hoang, B. M. Rosen and
V. Percec, J. Am. Chem. Soc., 2010, 132, 1800; (b) M. Tobisu,
Y. Kita, Y. Ano and N. Chatani, J. Am. Chem. Soc., 2008, 130,
15982; (c) K. Ukai, M. Aoki, J. Takaya and N. Iwasawa, J. Am.
Chem. Soc., 2006, 128, 8706.
c
1540 Chem. Commun., 2012, 48, 1538–1540
This journal is The Royal Society of Chemistry 2012