UPDATES
Mohammad Al-Amin et al.
was filtered through a Celite pad and concentrated under
vacuum. The residue was subjected to column chromatogra-
phy on silica gel (eluent: hexane/Et2O=80% to 75%) to
afford the desired alkynylated product 3a as a colorless oil;
yield: 44.7 mg [51% (90%)].
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À
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Typical Experimental Procedure for the SAuPd-
Catalyzed Alkynylation: SAuPd-Catalyzed Reaction
of Amide 1a with 2 (Table 3, entry 8)
To an oven-dried test tube, N-(8-quinolinyl)hexanamide 1a
(50.0 mg, 0.21 mmol), (bromoethynyl)triisopropylsilane
2
(50.0 mg, 0.19 mmol), SAuPd and xylene (1.5 mL) were
added under a gentle stream of argon. The mixture was
heated for 4 h at 1358C followed by cooling, SAuPd was re-
moved from the reaction mixture [the SAuPd was washed
with xylene (6ꢃ3.0 mL) and kept for next cycle]. The (bro-
moethynyl)triisopropylsilane
2
(30.6 mg, 0.18 mmol),
AgOAc (41.3 mg, 0.25 mmol) and LiCl (17.5 mg, 0.41 mmol)
were added into the above reaction mixture under a gentle
stream of argon. The mixture was stirred for 10 h at 1358C
and followed by cooling, the mixture was filtered through
a Celite pad and concentrated under vacuum. The residue
was subjected to column chromatography on silica gel
(eluent: hexane/Et2O=80% to 75%) to afford the desired
alkynylated product 3a as a colorless oil; yield: 46.6 mg
[53% (91%)]. The above reaction process was maintained
as for 2nd cycle and this procedure was repeated for a total
10 cycles.
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3
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Acknowledgements
This work was supported by a Grant-in-Aid for Scientific Re-
search on Innovative Areas “Molecular Activation Directed
toward Straightforward Synthesis” from the Ministry of Edu-
cation, Culture, Sports, Science, and Technology, Japan
(MEXT).
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[8] In these experiments, we used 1.2 cmꢃ1.4 cm, 100
mesh, SAuPd, which contained 50–100 mg of Pd.
6
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Adv. Synth. Catal. 0000, 000, 0 – 0
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