Science of Synthesis

Göttlich, R., Science of Synthesis, (2007) 25, 387.

The Meerwein arylation[‌118‌] is a copper-induced reaction of aromatic diazonium salts with alkenes. The reaction proceeds best with electron-deficient alkenes, such as α,β-unsaturated carbonyl compounds or styrenes.[‌119‌,‌120‌] The reaction involves a radical mechanism similar to that of the Sandmeyer reaction (‌Scheme 29‌).

‌Meeeee 88‌ Meeeeeee Meeeeeeee ee Meeeeeee[‌888‌,‌888‌]

Mee eeeeeeeee eee eeeeeeee eeeeee eeee eeeeee(M) eeeeeeee ee eeee eeeeee(MM) eeeeeeee eee ee eeee eeeeeee. Mee eeeeee eeee ee eee eeeeee eeee ee eeee e eeeeee eeeeeee eeee ee eeeeeee eeeeeeee ee eee eeeeee(MM) eeee ee eeee ee α-eeeeeeeeeeeeee, e.e. ‌88‌, eeee eeeeeeeeeeee eeeeeeeeeeee ee eee eeeeee(M) eeeeeee. Meeeeeee eeeeeeeee α,β-eeeeeeeeeee eeeeeeeee ee eee eeeeee eeeeeee eee eeee.

Mee eeeee eeee, eee eeeeeeee ee e eeeeeeee eeee ee eee α-eeeeeeee, eee ee eeeeeee ee ee eeeeee ee eeeeeeee(MMM) eeeeeeee ee eeee eeeeeee ee eee eeeeee eeee; eeeeeee, eeee eee eeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeeee eee eeee eeeeeeee, eeeeeee ee 8-eeeeeeeeeeeee (‌88‌) (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeee Meeeeeeee Meeee Meeeeeee(MMM) Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeeeeeeeeeee (‌88‌):[‌888‌,‌888‌]

M 8-M eeeee-eeeeee eeeee eeeeee eeee e eeeeeee, eeeeeeeeeee, eeeeeeee eeeeee, eee ee eeee eeee eeeeeee ee e eeeeee eeeeeee eee eeeeeee eeee eeeeeeee (88.8 e, 888 eeee), eeeeeee (888 eM), MeMe (88 e), eee MeM (8 e). Mee eeeeeee eee eeeeeeeeee ee 8–8°M eeeee e eeee ee MeM8+ Me− (8.88 eee), eeeeeeeeeee ee eM 8 eeee MeMMM8, eee eeeee eeee eee eeeeeeee eeeeee ee eeee e eeee eeee M8 eeeeeee ee 8–8 eeeeeee eee eeeeee. Mee eM eee eeeeeeeee eeeeee eee eeeeeeee, eeeeee eeeeeeeeeeee eeee e eM eeeee ee eeeeeeeeeeeeee eeee eM eeeee, eee MeMMM8 eee eeeee, ee eeeeeeee, ee eeeeeeee e eM ee 8–8. M8 eeeeeeeee eee eeeeeeee eeeee 8 e. Mee eeeeeee eee eeeeeeeee eeee Me8M, eee eee Me8M eeeee eee eeeeee eeee ee MeMe8. Mee eeeeeee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeee; eeeee: 88.8 e (88%); ee 888–888°M/88 Meee.

8-Meeeeeeeeeeee (‌88‌):[‌888‌]

M eeee ee MeMM8 (8.88 e, 88 eeee) ee M8M (88 eM) eee eeeee MMe (8 eM) eee eeeeeeeeee ee 8–8°M ee eeeee e eeee ee MeMM8 (8.88 e, 88 eeee) ee M8M (8 eM). Mee eeee eeeeeeeee eeee eeee eee eeeeee eeeee ee e eeeeeee eeeeeee ee e 88% eeeeee eeee ee MeMe8 (88 eeee) eee eeeeeee eeeeeeeee (M)-eee-8-eeee (88–88 eeee) ee eeeeeeeeeeee eeeeeee (88 eM) ee 88°M. Mee eeeeeeee eee eeeeeeeeee eee eee eeeeeeee eeee eee eeeeeeee ee eeee M8 eee eeeeeee ee 8–8 eeeeeee eee eeeeee (8.8–8 e). Mee eeeeeeeee eeeeeeeeee eeee eee eeeeeee eee 88 eee ee 88°M, eeeeeeeeeeee ee 88 eM eeeee eeeeeee eeeeeeee, eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee eeeeee ee eeeeeeeeeeee eeeee e eeeeeee eeeeeeee ee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.