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Please login or sign up for a free trial to access the full content. Method 2: Synthesis of Alkyl Aryl Selenides by Substitution

DOI: 10.1055/sos-SD-031-01173

Watanabe, S.; Kataoka, T.Science of Synthesis, (2007311135.

The preparation of alkyl aryl selenides is achieved through the cross-coupling reaction of diphenyl diselenide and alkyl halides. The desired compounds are obtained from ruthenium(III) chloride catalyzed reactions of diphenyl diselenide with alkyl bromides or iodides in the presence of zinc, in excellent yields (Scheme 53).[‌236‌]

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Meeeeeeeeee 88

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Me M 8°M, 8e 88 [‌888‌]
8-MeMM8M8 M 8°M, 88eee 88 [‌888‌]
8-MeMM8M8 M 8°M, 8e; eeee ee, 8e 88 [‌888‌]
8-Mee M ee, 8.8e 88 [‌888‌]
8-Mee M 8°M, 8.8e 88 [‌888‌]
Me Me ee, 88eee 88 [‌888‌]
8°M, 8e 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Mee-8-ee-8-ee Meeeee Meeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Meee e eee-eeeeee eeeee eeeeeeee eeee e eeeeee eeeeeeeee eee e eeeeeeee eeeeeeee eee eeee eeeeee Me(MMe)8 (8.88eeee), eeeeeeee (8.8eM), eee eeeeee (8.8eeee), eee MeMeM (8.88.8eeee) eeeee e M8 eeeeeeeeee. Mee eeeeeee eee eeeeee ee 888°M, eeee eeeeeeee, eee 88e. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeeee eee eeeeeee ee eeeeeeeeee (Meeeee) eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeeee eee eeeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, eeeeee/MeMMe); eeeee: 88888%.

Meeeeee Meeeee Meeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eee eeeeee (8.88eeee), (MeMe)8 (8.888eeee), eee MeM (8.88eeee) ee eeeeeeeeee, eeeeeee MMMM (8eM) eee eeeeeee ee ee eee 88 ee 88e. Meeee eeeeeee eeeeee eeeeee eee eeeeeeeeee eeee Me8M ee MM8Me8, eee eeeee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeeeeeee; eeeee: 8888%.

Meeeee Meeeee Meeeeeee (888, M8=Me); Meeeeee Meeeeeeee:[‌888‌]

MeMeM (88ee, 8.888eeee) eee eeeee ee e eeee eeeeeeeeee 8-Å eeeeeeeee eeeeee (888ee), MeMMM8M (888ee, 8.888eeee), eee eeeee MMM (8eM) eee eee eeee eeeeee eeeeeeeeee eee eeeeeeeeee eeeeeee eeeee e eee M8 eeeeeeeeee eee 8e ee ee. MeMe (888ee, 8.888eeee) eee eeeee ee eee eeeeeee, ee eeeee eeeee eee eeee eeeeee ee eeee eeeeee. Meeee 88e, eee eeeeeee eee eeeeeeee, eee eeeee eeeeeee eee eeeeee eeee Me8M (888eM), eee eee eeeeeeee eeeeeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeee eee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee) ee eeeeee e eeeee eeeeee eee; eeeee: 888ee (88%).

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M eeee ee 8-eeeee-8-eeeeeeeeeeeeee (8.88e, 8eeee) ee eeeee MM8Me8 (8eM) eee eeeee ee ee ee e eeeeeeeeee ee Me (888ee, 8eeee) eee (MeMe)8 (888ee, 8.8eeee) ee MM8Me8 (8eM). Mee eeeeeeeeee eee eeeeeee ee ee eee 8e. M8M (88eM) eee eeee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M (8×88eM) eee eeeeee eeee M8M (8×88eM). Mee Me8M eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee ee eeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee); eeeee: 8.88e (88%).