Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
31.19.6.1.2 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]

Meeeee 88 Meeeeeeee ee Meeee Meeeee Meeeeeeee eeee Meeee Meeeeee eee Meeeeeee Meeeeeeeee eeee e Meeeeeeee(MMM) Meeeeeee Meeeeeee[‌888‌]

Mee eeeeee eeeeeeeeeeeeee eeeeeeeee ee eeeeeee eeee eeeeeeeee 888 ee eeeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeee eeeeeee eeee eeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eee eeeeeeee (Meeeee 88).[‌888‌] Me eeee eeeeeeeeeeeeeee, eeeeeeee eee eee ee e eeeeeeee eeeeee eee eeeeee eeeeeeeee eeeeeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeee ee Meeeeeee Meeeeee[‌888‌]

Meeeeeeeeeeee eeeeeeee eeeeeeee eeeee eeee eeeee, eeeeeee, eee eeeeeee eeeeeeeeee ee eeeeeeee eeeeeeeeeeeee eeeee,[‌888‌‌888‌] eeeeeee,[‌888‌] eee eeeeeee[‌888‌‌888‌] eeee eeeeeeeee. Meeeee eeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeee eeee ee eeeeeeeeeeeee. Meeeeeee eeeee eeeeeeeeeeee ee 8,8-eee(eeeeeeeeeeeeee)-8,8-eeeeeeeeeeeee (888), eeeeeeee ee eeeeeeeee eeee eeeeeeee eeeeeeeeee, eeeee eee 8,8-eee(eeeeeeeeeeeee) eeeeeee, eeeee eee ee eeeeeee eeeeeeeeeee eeee eeeeeeeeeeee eeee ee eeeeee eee eeeeeeeeeeeee eeeeeeeeee eeeeeeeeee 888 (Meeeee 88).[‌888‌] Me eeeeeeeee eeeeeeeeeee ee eeeeeee eeee eeeeeeeee 888 ee eee eeeeeeee ee eeeeeeee eeeeeee eeee eeeeee(M) eeeeee eeeee eeeeeee eeeeeeeeee. Mee eeeeeee, eeeeeeee eeeeeeeeee eeeeee eeee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee ee eeeeeeee eeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeee(M) eeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee ee 88% eeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee Meee Meeee Meeeeeeee eee Meeeeee Meeeee Meeeeeeee eeee Meeeeeeeeee[‌888‌,‌888‌]

Meeee eee eeee eeeeee eeeeeeeee ee eee eeeeeeeee ee eeeee eeee eeeeeeeee ee eeeeeeeeeeee eeeeeeeee ee eeeee eeeeeee eeee eeeeeeeeeeeeeeee, ee eeee ee ee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee eeee eeeeeeeeeeeeeeeee.[‌888‌,‌888‌,‌888‌,‌888‌‌888‌] M eeeeeeeeee eee-eee eeeeee eee eee eeeeeeeee ee eeeee eeee eeeeeeeee eee eeee eeeeeeee. Meee, ee eee eeeeeeee ee eeeeee eeeeeeeee, eeeeeeeee eeeeee, eee eeeeeeeeeeeeeeeee, eeeeeeeeeeeeee eeeeeeeee eeeeee eeeeeeeeee eeee e eeeeeee ee eeeee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeee 888 ee eeee eeeeee (Meeeee 88).[‌888‌] Mee eeeeeeeeeee ee eeeeeeee eeeee eeeeeeeee ee eeeeeeeeeeee ee e eeeeeeee eeeee eeeee ee eee ee eeee eeee, eee eee eeeeee ee eee eeee-eeeeeeee eeeeeeeee ee eeeeeeee eeeee eeeeeeeee eeee eeeeeeee eeeee eeeeeee. Me eeee eee, eeee-eeeee eeeeee eeeeeeee ee eeeeeeeeeee eeeeeeee eeee eeee-eeeee eeeeee eee eeeeeeee eeeeeeeeee ee eee eeeeeeee ee eeee.[‌888‌]

Meeeee 88 Meeeeeeee ee Meeee Meeeee Meeeeeeee eeee Meeee Meeeeee eee Meeeeeeeeee[‌888‌,‌888‌]

Mee eeeeeee eeeeeeeeeee eeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeee eee eee eeeeee eeeeeeeeee ee eeeeeee eeeeeeee eeeeeee eeeeee eeee e eeeeeeeeeeeee eeeee eeeee eeee eeeeeeeeee, eee eeee eeeeeeeee. Meee, eeeeeeeee ee eeeeee eeeeeee eeeeeeeeeee 888 eeee eeeeee eeeeeeeeeeeeee eeeeeeee eee eeeeeeee eeeeeeeeee ee 8°M eeeeeee eeeeeeee ee eeeeeeee eee eeeeeeeeeeeee eeeeeeee 888 ee eeee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee Meeeee Meeeeeee eeee Meeeee Meeeeeeeeeeeee Meeeeeee eee Meeeeeee Meeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) Mee
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%).

8-Meeeeeeeeeeee Meeeee Meeeeeee [888, M8=MM8MMMe(MM8)8Me]; Meeeeee Meeeeeeee:[‌888‌]

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%).

References