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C. L. Smith et al.
LETTER
(13) Fang, A. G.; Mello, J. V.; Finney, N. S. Org. Lett. 2003, 5,
967.
Acknowledgment
Funding from the EPSRC (to C.L.S.), the Rotary Foundation (to
C.H.) and the National Science Foundation (Grant 0966420, to
D.J.N.) is acknowledged.
(14) Grushin V. V.; Organometallics; 2000, 19: 1888; a screen of
alternative phosphines [XPhos, PCy3, P(o-Tol)3, P(o-furanyl)]
was conducted (using 6a and 4-bromoanisole), but none
offered a significant advantage (in % yield) over Ph3P.
(15) Demers, S.; Stevenson, H.; Candler, J.; Bashore, C. G.;
Arnold, E. P.; O’Neill, B. T.; Coe, J. W. Tetrahedron Lett.
2008, 49, 3368.
References and Notes
(1) Irlapati, N. R.; Adlington, R. M.; Conte, A.; Pritchard, G. J.;
Marquez, R.; Baldwin, J. E. Tetrahedron 2004, 60, 9307.
(2) Mandal, D.; Yamaguchi, A. D.; Yamaguchi, J.; Itami, K.
J. Am. Chem. Soc. 2011, 133, 19660.
(3) Croxtall, J. D.; Keam, S. J. Drugs 2009, 69, 1059.
(4) Goodyear, M. D.; Hill, M. L.; West, J. P.; Whitehead, A. J.
Tetrahedron Lett. 2005, 46, 8535.
(5) Marcaurelle, L. A.; Johannes, C.; Yohannes, D.; Tillotson,
B. P.; Mann, D. Bioorg. Med. Chem. Lett. 2009, 19, 2500.
(6) Rouden, J.; Lasne, M.-C.; Blanchet, J.; Baudoux, J. Chem.
Rev. 2014, 114, 712.
(16) Harrison, I. T. J. Chem. Soc. D 1969, 616a.
(17) Feutrill, G. I.; Mirrington, R. N. Tetrahedron Lett. 1970,
1327.
(18) Representative 1H NMR Data
2-Methoxy-6-(2-methoxyphenyl)pyridine (19c)
1H NMR (400 MHz, CDCl3): δ = 7.97 (dd, J = 7.5, 2.0 Hz, 1
H), 7.61 (t, J = 7.5 Hz, 1 H), 7.55 (dd, J = 7.5, 1.0 Hz, 1 H),
7.37 (ddd, J = 8.5, 7.0, 1.5 Hz, 1 H), 7.09 (td, J = 7.5, 1.0 Hz,
1 H), 7.01 (dd, J = 8.5, 1.0 Hz, 1 H), 6.68 (dd, J = 7.5, 1.0
Hz, 1 H), 4.01 (s, 3 H), 3.89 (s, 3 H).
4-Methoxy-2-(4-methoxyphenyl)pyrimidine (21b)
1H NMR (400 MHz, CDCl3): δ = 8.45 (d, J = 5.5 Hz, 1 H),
8.40 (d, J = 9.0 Hz, 2 H), 6.98 (d, J = 9.0 Hz, 2 H), 6.56 (d,
J = 5.5 Hz, 1 H), 4.07 (s, 3 H), 3.88 (s, 3 H).
2-(Benzyloxy)-6-(thien-2-yl)pyrazine (24d)
1H NMR (400 MHz, CDCl3): δ = 8.53 (br s, 1 H), 8.13 (br s,
1 H), 7.66 (dd, J = 4.0, 1.0 Hz, 1 H), 7.53 (d, J = 7.5 Hz, 2
H), 7.46 (dd, J = 5.0, 1.0 Hz, 1 H), 7.31–7.42 (m, 3 H), 7.14
(dd, J = 5.0, 4.0 Hz, 1 H), 5.48 (s, 2 H).
(7) Honda, T.; Takahashi, R.; Namiki, H. J. Org. Chem. 2005,
70, 499.
(8) Hirschhäuser, C.; Haseler, C. A.; Gallagher, T. Angew.
Chem. Int. Ed. 2011, 50, 5162.
(9) The instability of 2-pyridyl boronic acids and
trifluoroborates, and the propensity of electron-deficient
boronic acids toward homocoupling have been described,
see: Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68,
4302.
(10) (a) Sandosham, J.; Undheim, K. Tetrahedron 1994, 50, 275.
(b) Sandosham, J.; Undheim, K. Acta Chem. Scand. 1989,
43, 684.
6-(Thien-2-yl)pyridin-2(1H)-one (27)
1H NMR (400 MHz, CDCl3): δ = 12.82 (br s, 1 H), 7.98 (d,
J = 3.5 Hz, 1 H), 7.43 (t, J = 8.5 Hz, 1 H), 7.38 (d, J = 5.0
Hz, 1 H), 7.16 (dd, J = 5.0, 3.5 Hz, 1 H), 6.52 (d, J = 8.5 Hz,
2 H).
(11) Darabantu, M.; Boully, L.; Turck, A.; Plé, N. Tetrahedron
2005, 61, 2897.
(12) Majeed, A. J.; Antonsen, Ø.; Benneche, T.; Undheim, K.
Tetrahedron 1989, 45, 993.
2-Phenylpyrimidin-4(3H)-one (29)
1H NMR (400 MHz, CDCl3): δ = 8.19 (dd, J = 8.0, 1.5 Hz, 2
H), 8.15 (d, J = 6.5 Hz, 1 H), 7.52–7.61 (m, 3 H), 6.46 (d,
J = 6.5 Hz, 1 H).
Synlett 2014, 25, 1904–1908
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