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2.1.5.1.3 N-Alkynylation of Sulfonamides and Intramolecular Cyclizations of Alkynyl Sulfonamides

DOI: 10.1055/sos-SD-208-00158

Duan, J.; Chen, H.; Hong, X.; Harmata, M.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132259.

Various N-alkynylsulfonamides 10 can be prepared in good to excellent yields from haloalkynes and aliphatic or aromatic sulfonamides 9 in the presence of catalytic amounts of copper(I) iodide. Open-chain N-benzyl-4-toluenesulfonamide is smoothly alkynylated with 1-bromooct-1-yne to give N-benzyl-N-(oct-1-ynyl)-4-toluenesulfonamide [10, R1 = 4-Tol; R2 = Bn; R3 = (CH2)5Me] in 93% yield (Scheme 6). More sterically demanding sulfonamides are alkynylated equally well to afford the desired products. The enantiopurity of an optically active sultam is completely retained in the product.[‌31‌]

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Meeeeeeeeee 8

M8 M8 M8 Meeee (%) Mee
8-Mee Me (MM8)8Me 88 [‌88‌]
8-Mee Me MMM 88 [‌88‌]
(MM8)8Me 88 [‌88‌]
MMM 88 [‌88‌]
(MM8)8Me 88 [‌88‌]
MMM 88 [‌88‌]
(MM8)8Me 88 [‌88‌]
MMM 88 [‌88‌]
(MM8)8Me 88 [‌88‌]
MMM 88 [‌88‌]

Meeeeeeeeeeeee 8-eeee-eee eeeeeeeeeee ee eeeeeee eeeeeeeeeeee 88 eeeee e eeeeeeeee eeeeee ee eeeeeeeeeee eeeeeeeee 8-eeeeeeeee eeeeeee 88 ee eeee eeeeee.[‌88‌] Meeeeee eee eeeeeeee eeeeee ee eee eeee eee eeee eeeeeeeee ee M-eeeeeeeeeeee eeeeeeeeeee eee eeee eeeeeeeee (Meeeee 8).

Meeeee 8 Meee-Meeeeeeee Meeeeeeeeee ee 8-Meeeeee-M-eeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 M8 Meee (e) Meeee (%) Mee
Me Me M 8 88 [‌88‌]
Me M M 8 88 [‌88‌]
Me M M 8.8 88 [‌88‌]
Me Me M 8.8 88 [‌88‌]
Me Me MM8 8 88 [‌88‌]
Me M M 8 88 [‌88‌]
M M M 8 88 [‌88‌]
MM8MM M M 8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-eeee-Meeee-M-(eee-8-eeee)-8,8-eeeeeee-8,8-eeeeeeeeeeeeeee 8,8-Meeeeee [88, M8,M8 = MMe-MeM8M8; M8 = (MM8)8Me]; Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeeeeeeee eeeeeee ee 8-eeee-eeeee-8,8-eeeeeee-8,8-eeeeeeeeeeeeeee 8,8-eeeeeee (8, M8,M8 = MMe-MeM8M8; 88.8 ee, 8.888 eeee), eeeeeeee M8MM8 (888 ee, 8.88 eeee), eee MeM (8.8 ee, 8.888 eeee) ee eeeeeee (8 eM) eee eeeee 8-eeeeeeee-8-eee (88.8 ee, 8.888 eeee) ee eeeeeee (8 eM) eeeeeeee ee M,M′-eeeeeeeeeeeeeeeeeeeeeee (MMMMM; 8.888 eM) eeeee ee eeeee eeeeeeeeee. Mee eeeeeee eee eeeeeee eeeeeeeee ee 888 °M (eee eeee). Me eee eeee eeeeee ee ee eee eeeeeeee eeeeeee e eeeee eee ee eeeeee eee, eeeee eee eeeeee MeMMe. Mee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eee, eeeee eee eeeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe) ee eeee eee eeeee eeeeeeee ee ee eee; eeeee: 888.8 ee (88%).

8-Meeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me8Me (8.88 eeee) eee eeeee ee e eeee ee eee eeeeeeeeeee 88 (8.8 eeee) ee eeeee eeeeeee (8 eM). Mee eeeeeee eee eeee eeeeeee ee eeeeee eee 8–8 e. Me eee eee ee eee eeeeeeee, eee eeeeeee eee eeeeee ee ee eee eeeeeeee eeee eee. MM8Me eeee (8 eM). Mee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM), eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) eeeeeeee 88.

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