1
870
M. Murata et al.
LETTER
References and Notes
(12) For a review of the palladium-catalyzed couplings of aryl
chlorides, see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed.
(
1) For reviews of the Suzuki coupling, see: (a) Miyaura, N.;
Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Miyaura, N.
Adv. Organomet. Chem. 1998, 6, 187. (c) Miyaura, N. Top.
Curr. Chem. 2002, 219, 11.
2
002, 41, 4176.
1
(
13) Compound 3d: H NMR (CDCl ): d = 1.35 (s, 12 H), 7.47 (t,
3
J = 7.9 Hz, 1 H), 7.73 (d, J = 7.9 Hz, 1 H), 8.01 (d, J = 7.9
13
Hz, 1 H), 8.09 (s, 1 H). C NMR (CDCl ): d = 24.81, 84.46,
3
(
(
(
2) For reviews of the Miyaura borylation, see: (a) Ishiyama,
111.95, 118.79, 128.36, 134.37, 138.37, 138.73. HRMS
T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.
+
(
EI): m/z calcd for C H BNO [M ]: 229.1274; found:
13 16 2
(
b) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271.
3) (a) Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem.
997, 62, 6458. (b) Murata, M.; Oyama, T.; Watanabe, S.;
–1
229.1312. IR (KBr): 2228 cm .
1
Compound 3f: H NMR (CDCl ): d = 1.36 (s, 12 H), 7.61 (d,
J = 7.9 Hz, 2 H), 7.92 (d, J = 7.9 Hz, 2 H). C NMR
3
1
13
Masuda, Y. J. Org. Chem. 2000, 65, 164.
(
CDCl ): d = 24.98, 84.25, 124.29 (q, J = 4 Hz), 124.13 (q,
3
4) (a) Murata, M.; Watanabe, S.; Masuda, Y. Tetrahedron Lett.
J = 272 Hz), 132.80 (q, J = 32 Hz), 135.21. HRMS (EI):
m/z calcd for C H BF O [M ]: 272.1196; found:
2000, 41, 5877. (b) Murata, M.; Oyama, T.; Watanabe, S.;
+
1
3
16
3
2
Masuda, Y. Synthesis 2000, 778. (c) Murata, M.; Oyama,
T.; Watanabe, S.; Masuda, Y. Synth. Commun. 2002, 32,
2
72.1229.
1
Compound 3g: H NMR (CDCl ): d = 1.21 (s, 12 H), 7.30–
3
2
513.
5) Baudoin, O.; Guénard, D.; Guéritte, F. J. Org. Chem. 2000,
5, 9268.
6) Doux, M.; Mézailles, N.; Melaimi, M.; Ricard, L.; LeFloch,
P. Chem. Commun. 2002, 1566.
13
7.50 (m, 8 H), 7.71 (d, J = 7.8 Hz, 1 H). C NMR (CDCl ):
3
(
(
(
(
(
d = 24.55, 83.69, 126.23, 126.79, 127.74, 128.92, 129.08,
6
1
30.03, 134.40, 143.19, 147.46. HRMS (EI): m/z calcd for
+
C H BO [M ]: 280.1635; found: 280.1629.
Compound 3i: H NMR (CDCl ): d = 1.21 (d, J = 6.7 Hz, 6
H), 1.25 (d, J = 6.7 Hz, 12 H), 1.37 (s, 12 H), 2.84 (sept,
1
8
21
2
1
3
7) Wolan, A.; Zaidlewicz, M. Org. Biomol. Chem. 2003, 1,
3274.
J = 6.7 Hz, 1 H), 2.98 (sept, J = 6.7 Hz, 2 H), 6.93 (s, 2 H).
8) Broutin, P.-E.; Čerña, I.; Campaniello, M.; Leroux, F.;
Colobert, F. Org. Lett. 2004, 6, 4419.
9) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397.
13
C NMR (CDCl ): d = 24.01, 24.55, 24.98, 34.00, 34.49,
3
83.61, 119.63, 149.72, 151.86. HRMS (EI): m/z calcd for
+
C H BO [M ]: 330.2730; found: 330.2773.
Compound 3j: H NMR (CDCl ): d = 1.32 (s, 12 H), 2.86 (d,
J = 5.5 Hz, 3 H), 3.92 (br s, 1 H), 6.58 (d, J = 8.5 Hz, 2 H),
2
1
35
2
(
10) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120,
369.
11) t-Bu-DPEphos (L8) was prepared from diphenylether and
t-Bu) PCl by a similar procedure for the preparation of
1
3
7
(
13
7
.65 (d, J = 8.5 Hz, 2 H). C NMR (CDCl ): d = 24.79,
3
(
2
30.22, 83.13, 111.38, 136.26, 151.74. HRMS (EI): m/z calcd
DPEphos. See: Kranenburg, M.; Vanderburgt, Y. E. M.;
Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.;
Fraanje, J. Organometallics 1995, 14, 3081.
+
for C H BNO [M ]: 233.1587; found: 233.1611.
IR (KBr): 3425, 3401, 3375 cm .
1
3
20
2
–1
Synlett 2006, No. 12, 1867–1870 © Thieme Stuttgart · New York