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N. Riemer et al.
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The diazonium salt 3f (134 mg, 0.50 mmol), triarylbismuthane
7c (265 mg, 0.50 mmol, 1.0 equiv), Pd(acac)2 (15.2 mg, 0.05
mmol, 10 mol%), and NaOAc (123 mg, 1.50 mmol, 3.0 equiv)
were suspended in MeCN (0.5 mL, 1.0 M), and the mixture was
stirred for 16–18 h at r.t. The mixture was then diluted with
EtOAc (30 mL), washed with H2O (30 mL), dried (MgSO4), and
concentrated in vacuo. The crude product was purified by
column chromatography (silica gel, PE-–EtOAc) to give a color-
less oil; yield: 66 mg (51%, 0.26 mmol).
IR (ATR): 2999 (bw), 1738 (w), 1675 (m), 1204 (s), 1170 (m) cm–1
.
1H NMR (500 MHz, CDCl3): δ = 10.78 (s, 1 H), 8.07 (d, J = 2.2 Hz,
1 H), 7.70 (dd, J = 8.6, 2.2 Hz, 1 H), 7.35 (t, J = 7.9 Hz, 1 H), 7.13
(d, J = 7.7 Hz, 1 H), 7.09–7.03 (m, 2 H), 6.88 (dd, J = 8.2, 2.2 Hz, 1
H), 3.98 (s, 3 H), 3.87 (s, 3 H). 13C NMR (126 MHz, CDCl3):
δ = 170.7, 161.2, 160.2, 141.6, 134.6, 132.4, 130.0, 128.4, 119.3,
118.2, 112.7, 112.6, 112.4, 55.5, 52.5. HRMS (ESI): m/z [M + Na]+
calcd for C15H14NaO4: 281.0784; found: 281.0787.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E