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LETTER
General Procedure in Toluene (Table 2, Entry 1)
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Into a test tube charged with CoCl2(PPh3)2 (13 mg, 0.02 mmol, 10
mol%) in toluene (0.2 mL) under nitrogen, aldehyde (0.2 mmol),
amine (0.24 mmol), alkyne (0.3 mmol), and 4 Å MS (50 mg) were
added. The tube was then stoppered. The reaction mixture was
stirred at 70 °C (oil bath temperature) for 24 h. After cooling to r.t.,
the reaction mixture was filtered through Celite in a pipette eluting
with EtOAc. The volatile was removed under vacuum, and the res-
idue was purified by flash column chromatography on silica gel
(eluent: hexane–EtOAc = 20:1 to 10:1) to give the corresponding
product 4a in 91% isolated yield as a yellowish oil. 1H NMR (400
MHz, CDCl3): d = 7.67–7.63 (m, 2 H), 7.55–7.50 (m, 2 H), 7.39–
7.28 (m, 6 H), 4.83 (s, 1 H), 2.60–2.50 (m, 4 H), 1.70–1.50 (m, 4 H),
1.50–1.40 (m, 2 H). 13C NMR (100 MHz, CDCl3): d = 138.5, 131.8,
128.5, 128.2, 128.0 (two signals overlap), 127.4, 123.3, 87.8, 86.0,
62.3, 50.6, 26.1, 24.4. A similar procedure was carried out in
CH2Cl2 at r.t.
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Acknowledgment
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(b) Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.;
We are grateful to the Canada Research Chair (Tier I) Foundation
(C.J.L.), the CFI, NSERC, and ACS-Green Chemistry Pharmaceu-
tical Roundtable for the support of our research.
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