Table 1.

Synthesis of Quinolines from N-(2-Alkynyl)triflamides^a

entry	triflamide		electrophile	product		% overall yield
1		1	ICl		2	88
2		3	ICl		4	62
3		5	ICl		6	45
4		7	ICl		8	51
5		9	ICl		10	trace
6		9	I2/AgClO4		10	trace
7		11	ICl		12	25
8		13	ICl		14	trace
9		15	ICl			60+25
10		18	ICl		19	56
11		20	ICl		2	74

^aAll reactions were run using 0.30 mmol of the N-(2-alkynyl)sulfonamide and 1.5 equiv of ICl in 3 mL of CH₂Cl₂ at −78 °C for 1 h. After work-up, the solvent was removed, the crude mixture and 10 equiv of NaOMe were directly dissolved in MeOH and stirred overnight.