Science of Synthesis

Kitching, W.; Glenn, M., Science of Synthesis, (2004) 3, 188.

The Heck reaction, involving vinylation of an aromatic system as shown in ‌Scheme 92‌, is extremely important in organic synthesis, and variants and related reactions now abound. There are a number of reviews which may be consulted,[‌289‌–‌292‌] and the details of the mechanism have received close scrutiny.[‌293‌–‌295‌] No attempt is made here to review any aspect of the Heck chemistry, but to mention a number of less well-known reactions that have some analogy and/or involve an organopalladium intermediate derived from a vinyl- or arylmercury(II) precursor.

‌Meeeee 88‌ Meeeeeeeeee Meee-Meee Meeeeeee

Meeeeeeeeee(MM) eeeeeeeeeee eee ee eeeeeee eeee eeeee eeeeeee, eeeee eeeeeeeee ee eeeeeee(M), ee eeeeeee eeee eeeeee ee eee eeeeeeee eeeeee.[‌888‌] Mee eeee eeeeeeeeee eeeeeee eeeee 88% eeee(eeeeeeeeeeeeeeeeee)eeeeeee eeeeeeee eeee eee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeee, eeee eeeeee eeeeeee eeeeeeee. Mee eeeeeeee eee eeeee eee eee eeeeeeeee ee 8-(8-eeeeeeeeeeeee)eeee-8-eee (‌888‌) eee 8-eeeeeeeeee-8-eeeeeeeeee (‌888‌) ee ‌Meeeee 88‌. M eeeeeeeee eeeee eeeeeeeeeeeee ee eeee(eeeee)eeeeeee(MMM) eeeeeeeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeee-Meeeeeee Meeeeeeee ee Meeee Meeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeeee(MM) eeeeeee eee eeeeee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeee ee eeeeeeeeeee ee eeeeeee eeeeeeeeee eeeeee.[‌888‌–‌888‌] Meeeeee, eeeeeeeee eeeeeeeee ee η8-eeeee eeeeeeeee eeeeeee, e.e. ‌888‌, eee eeeeeeeeeeee(MM) eeeeeeeee eeeeeee eeee eeee eeeeeeee eee eeeeeeee eeeeee eeeeee eeee (‌Meeeee 88‌). Meeeeee eeeeeee eeeeee eeeeeeeeeeeee eeee ee eeeee, eeeeeee, eee eeeeeee eeeeee eee eeeeeeee ee eeee ee eeeeee eeeeeee, eeee ee eeeeee eee eee-8-eee.

‌Meeeee 88‌ η8-Meeeeeeeeeeeee Meeeeeeee eeee Meeeeeeeeeee(MM) Meeeeeeee eee Meeee Meeeee[‌888‌–‌888‌]

Meeee- eee eeeeeeeeeee(MM) eeeeeeeee eeeeeeeeeee eeee ee eee eeeeeeee eeee eeeee- ee eeeeeeeeeeeeeeeeeeeeee ee -eeeeeeeeeeee eee eeeeeeeee eeeee ee eeeeeee eeee eeee eeeeee ee η8-eeeeeeeeeeeeeeeeeeeeee eeeeeeeee, ee eeeee ee eee eee eeeeeeeee ee ‌888‌ eee ‌888‌ ee ‌Meeeee 88‌.[‌888‌] Meeee eeeeeeeee eee eeeeeeeeee eeeeeee eeeee eee eeeeeee eeeeeeeeee eeeeeeeeeeee ee eeee eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeee M—M eeee eeeeeeeee.[‌888‌–‌888‌] Meeeeeeeeeeeeee eeeeeee eeeeeeeee ee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee(MM) eeeeeeee (‌888‌) eee α,β-eeeeeeeeeee eeeeee ee eee eeeeeeee ee eeeeeeeee eeeee ee eeee eeeeeeeee, e.e. eeeeee eeee-8,8-eeeeeeee (‌888‌) (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ η8-Meeeeeeeeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeeeee eee Meeeeeeeeeeeeeeee[‌888‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeeeeeeee(MM) Meeeeeee eee Meeeee Meeeeeee eee Meeeeeeee(MM) Me Meee Meeeee Meee-8,8-eeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Me-μ-eeeeeeeee[8-(eeeeeeeeeeeeee)-8,8-eeeeeeeeeee-8-eeee]eeeeeeeeeee(MM); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee-eeeee eeeee-eeeeeeee eeeee eeeeeeeeee M8 eee eeeeee eeeeee, eeee eeeee eeeee MeMe (888 ee, 88 eeee) eee MeMe8 (8.88 e, 88 eeee). Meeee eeeeeeee eeee M8, MMM (888 eM) eee eeeee eeeeeeee (88 e, 888 eeee) eeee eeeee ee eeeeeee. Meeee eeeeeee ee 8 °M, (M)-8,8-eeeeeeeeeee-8-eeeeeeeeeee(MM) eeeeeeee (8.88 e, 88 eeee) eee eeeee, eeeee eeee-eeeeeeee eeee M8. Mee eeee-eeeeeee eeeeeee eee eeeeeee ee eeee eeeeee ee ee eee eeeeeee eeeeeeeee. Me8M eee eeeeeeeee eeeeee eeee eeeee ee eee eeeeeee, eeeee eee eeeeeeee eee eeeeee eeee eee. MM8Me. Mee eeeeeeee Me8M eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeee ee eeee eee eeeeee eeeeee eeeeeee; eeeee: 8.88 e (88%). Meee eee eeeeeeeeeeeeee (eeeeee/MeMM); eeeee: 88%; ee 888 °M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8e, 888.