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. Author manuscript; available in PMC: 2010 Apr 16.
Published in final edited form as: Org Lett. 2009 Apr 16;11(8):1861–1864. doi: 10.1021/ol900434k

Table 2.

One-pot synthesis of 2,3-disubstituted thiophenes from 2-TBS-3-formylthiophene 2b.

Entry R-M E Product(yield) Entry R-M E Product(yield)
1 n-BuLi i-Pr-CHO graphic file with name nihms149962t12.jpg 5 Ph-Li Ph-CHO graphic file with name nihms149962t13.jpg
2 n-BuLi Ph-CHO graphic file with name nihms149962t14.jpg 6 graphic file with name nihms149962t15.jpg Ph-CHO graphic file with name nihms149962t16.jpg
3 n-BuLi (Ph)2CO graphic file with name nihms149962t17.jpg 7 graphic file with name nihms149962t18.jpg i-Pr-CHO graphic file with name nihms149962t19.jpg
4 Ph-Li MeI graphic file with name nihms149962t20.jpg 8 n-BuLi MeI graphic file with name nihms149962t21.jpg

Condition: Step 1: 2b (1.0 eq.), Nucleophile (1.1 eq.), THF, −78 °C, 30 min;

Step 2: DMPU/THF = (1/1), Electrophile (1.5 eq.), −78 °C to RT, 3 h

a)

We also obtained O-methylation product (15 i) in 41%