V. Vashchenko et al. / Tetrahedron Letters 49 (2008) 1445–1449
1449
XIX Ukrainian Conference for Organic Chemistry, Lviv, Ukraine,
September 10–14, 2001; Lvivs’ka politechnika: Lviv, Ukraine, 2001; p
134.
132.43, 131.96, 129.41, 127.18, 117.39, 58.02, 18.99; MS (%): m/z 253
(M+, 94), 200 (19), 183 (100), 155 (25), 75 (33). Anal. Calcd for
C
10H8BrNO2: C, 47.27; H, 3.17; N, 5.51. Found: C, 47.16; H, 3.24; N,
5. Similar methodology was used recently for the case of bicyclic
aziridines: Zbruyev, A. I.; Vashchenko, V. V.; Andryushchenko, A.
A.; Desenko, S. M.; Musatov, V. I.; Knyazeva, I. V.; Chebanov, V. A.
Tetrahedron 2007, 63, 4297–4303.
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5.65.
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21. General procedure for the reaction in microemulsion. A mixture of an
aryl halide (2 mmol), NaHCO3 (500 mg, 6 mmol, 3 equiv), SDS
(75 mg), water (5 ml) and toluene (2.5 ml) was degassed and flushed
with argon. Then, PdCl2(dppf) (44 mg, 0.06 mmol, 0.03 equiv) was
added under argon and the degassing was repeated. The resultant
emulsion was heated to reflux with stirring, and the areneboronic acid
(2.4 mmol, 1.2 equiv) in n-butyl alcohol (0.7 ml) and toluene (2.5 ml)
was added dropwise over 5–10 min. The reaction mixture was stirred
at reflux until HPLC revealed that the reaction was complete. The
reaction was then allowed to cool. The organic layer was separated,
the water layer was extracted with toluene, the extracts were collected,
washed with water and dried. In the case of base-insensitive materials,
the reaction mixture was cooled, diluted with isopropyl alcohol
(100 ml), evaporated to dryness and suspended in dichloromethane
(25 ml). The resultant suspension was filtered through a short pad of
silica, washed with dichloromethane (30 ml) and evaporated to
dryness. The product obtained was purified by crystallization from
an appropriate solvent.
22. Procedure for the quantitative experiment. PdCl2(dppf) (44 mg,
0.06 mmol, 0.03 equiv) was added to a well-degassed mixture of an
areneboronic acid (2.4 mmol, 1.2 equiv) and 75 mg of SDS (if
appropriate), in n-butyl alcohol (0.7 ml), water (2 ml), and benzene
(5 ml) under a flow of argon. Then, the aryl bromide (2 mmol,
1 equiv, neat or as a concentrated benzene solution) was added,
followed by an appropriate internal standard (4-substituted biphenyl
(C5H11 or OC9H19), 1.6 mmol, 0.8 equiv). The reaction mixture was
bubbled with argon while the bromide was added through a rubber
septum via a syringe. The reaction mixture was then degassed and
heated to reflux with stirring. A solution of sodium carbonate
decahydrate (1.7 g, 6 mmol, 3 equiv) in water (3 ml) was thoroughly
degassed by bubbling with argon and added quickly through the
rubber septum into the reaction mixture via a syringe. A sample of the
reactants was taken after a period of time measured from the addition
of the base (Table 2).
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C.; Reisner, A.; Jones, P. G. Angew. Chem., Int. Ed. Engl. 1995, 34,
1485–1488; (b) Andersen, N. G.; Maddaford, S. P.; Keay, B. A. J.
Org. Chem. 1996, 61, 9556–9559.
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Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158–163.
16. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207–210.
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Sect. A 2003, 401, 111–122.
18. Muller, H.; Tschierske, C. J. Chem. Soc., Chem. Commun. 1995, 645–
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19. This compound was obtained by dehydration of the corresponding
amide as described by Chan, L. K. M.; Gray, G. W.; Lacey, D.;
Scrowston, R. M.; Shenouda, I. G.; Toyne, K. J. Mol. Cryst. Liq.
Cryst. 1989, 172, 125–146. Representative data for 2d: mp 110–
25
111 °C; ½aꢀD ꢁ14.6 (c 0.04, CHCl3); 1H NMR (400 MHz, CDCl3): d
7.91 (d, J = 8.6 Hz, 2H), 7.62 (d, J = 8.5 Hz, 2H), 5.64 (q, J = 6.8 Hz,
1H), 1.78 (d, J = 6.8 Hz, 3H); 13C NMR (125 MHz, CDCl3): d 164.09,