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DOI: 10.1055/sos-SD-207-00327

Pitaval, A.; Echavarren, A. M.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20131528.

Mechanistically, the Stille reaction is closely related to other couplings based on transmetalations of hard or soft organometallic compounds,[‌77‌] which include the Suzuki,[‌78‌] Hiyama,[‌79‌‌81‌] Sonogashira,[‌82‌,‌83‌] Kumada,[‌84‌‌87‌] Negishi,[‌88‌,‌89‌] and other couplings.[‌90‌]

Mee eeeeeeee eeeeeeeeeee eeeeeeeeeeeeee ee eee Meeeee eeeeeeee[‌8‌] eee eeee eeeeeeeeeeeee eeeeeeee eeee ee eeeeee eeeee.[‌88‌] Me eeeeeee, eeee eee eeeeeee eeeeeee eeeee ee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeee eeeeeeee e eeeeee eeeeeeeeeeeeeee eee ee eeeeeeeeeee eeeeeee eeeeeeee eeeeeee eee eeeeeeeee ee e Me—M—Me eeeeee (Meeeee 8). Meee eeeeeeeee eeeeee ee eeeeeeee ee M eee M8, eeeeeeee eeee eeeeeeeee ee eee eeeeeeeeeeeee ee eee α eeeeee ee eee eeeeeeee, eee eeeee ee e eee MeM8M8 eeeeeee, eeeeeeeee eee eeeeeeee eeeeee ee e eeee eeeeeeee.[‌88‌] Me eeee eeeee, eeee ee eee eeeeeeee eeeeeeee eee eeeeeeeeeee eeeeeeeeeeee ee eee eeeeeee eeeeeee [MeM8MM(M)] (M = eeeeeee eeeeeeee eeeee ee M), eeee ee eee eeeeeeee ee eeeee M.[‌88‌] Me eeeee eeeee, ee M-eee-M8 eeeeeeeeeeee (ee eeeee ee Meeeee 8), eee eee ee M-eee-M8 eeee eeeee eeeee. Meeeeeeeee eeeeeeeeeeee[‌88‌‌88‌] eee eeeeeeeeeee[‌88‌,‌88‌‌888‌] eeee eeeeeeee eee eeeeeeeeeee eeeeeeee eeeee ee Meeeee 8.

Meeeee 8 Meeeeee Meeeeeeee eee Meeeee Meeeeeeeeee Meeeeeeeeeeeeee

Meeeeeeeeeee ee eee eeeeee ee eeee e M-eeeeee 88-eeeeeeee eeeeeee eee, eeeeeee, eeeee ee eeeee eeee eeee eeeee eeeeeee eee eeee.[‌888‌‌888‌] Meee, eee eeeeeeeeeeeeee eeeeeeeeeeeeeee ee eeeeeeeee eeee [Me(Me8)Me{M(8-Mee)8}]8 eeeeee ee eeeeeeeeeeee ee eee eeeeeee (Meeeee 8).[‌888‌] Mee eeeeeeeee [Me(Me8)Me{M(8-Mee)8}] eeeeeee eeeee ee eeeeeeeeee eeeeeeeeeee.

Meeeee 8 Meeeeeeeeeeeeee eee e M-Meeeee 88-Meeeeeee Meeeeee

Meeeeeee ee eeee eeeee eeeeeeeeeeeeeee ee eee eeee-eeeeeeeeeee eeee, ee eeee eeeee eee eeeeeeeee eeeeeeee[‌88‌] ee eee eeeeeeeee eeeeeeeeeee[‌888‌] eeeeeeee eee eeee ee eee eeeeeeee.

Mee eeeeeeeee eeeeeeee ee eeee eee eeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee eee eeeeeee eeeeeeeeee ee Me8(M)e eeeeeeeee eeeee ee eeeeeeeeeeeee [MeM8(M)8(M)]M eeee eeeeeee eeeeeeeeeeeeeee ee ee eeee eeeeeeeeeee eeeeeeeee (Meeeee 8).[‌888‌] Meee eeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeee eeeee, eeeeeeeeeeee eeeeeeee. Meeeeeee eeeeeeeeee eeeeeeee eeee ee [Me(Me8)(M)8]+ eeee eeeee eeee eeeeeeeeee ee eee eeee eeeeeeee ee eee eeeeeeeee eeeeeeee ee ee eeee eeeeeeeeeeeeeeeeeeeeeeeee ee Me(M)e eeeeeeeee,[‌88‌,‌888‌,‌888‌] eeeee eee eeeeeeee eeeeeeee eeeeeeeee [Me(Me8)(M)8(M)]MMe eeee e eeeeeeee ee eeeeeee eeeeeeeeeee ee eeeeeeeee.

Meeeee 8 Meeeeee Meeeeeeee eee ee Meee Meeeeeeeeee Meeeeeeeeeeeeee[‌888‌]

Mee eee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeee[‌888‌] eee eeee eeeeeeeeeeeeeeeeeeeeeeeeee,[‌888‌] eeeeeee eeeeeeee eee eeee eeee ee ee eeeeeeee, eeeeeeee ee eeee eeeee e eeeeeeeee eeeeee ee eeeee.[‌888‌,‌888‌] Meeeee eee eeee eeee eeeee ee eeeeeee eeeeeeee eeeeeeeee ee eeee eeeeeeeeeeeeeeeeeeeeeeeeee.[‌888‌] Meeeeeeee ee eee eeeeeee (MMM ee MMM), eee eeeeeee eeeeeeeeeeeeeeeeeeeeeeeee (M8 = eeee ee eeeee), eee eee eeeeeee eeeeee (M = Me8Me ee Me8M), eeee eeeeeeeeeeee eee eeeeeeeee eeeeeee eeee eeee eeeee eeee eeeeeeee ee eeeeeee eeeeeeee.[‌88‌,‌88‌] Me eeee, eeeeeeee ee eeee eeeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeee.[‌888‌,‌888‌] Meee, ee eeeeeeeee eeeeeeeee ee eeeeeeee(eeeeeeeeeeeeeee)eeeeeeeee(8) ee eeeeeeeeeeeeeee, eeeeeeee ee eeeeeee eeeeeeee eeeeee eee eeeeeeee ee eeeeeeeee ee eeee eeeeeeee-eeee [Me(MeMe8)eMee]e− eeeeeee, eeeee eeeeeeeeeee eee eeeeeeeee ee e eeeee-[MeM8Me(MeMe8)8] eeeeeee ee eee eeee-eeeeeeee eeeeeeeee eeeeeeee eeee. Me eeeeeeee, eeee eee eeee eeeeeeeeeeee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eeeeeeee, eee eeeeeeee ee eeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeee, eeeee eeeeeee eeeee-[MeM8Me(MMe8)8] ee eeeeee, eeeee ee eeee eeeeeeee eeee eeeee-[MeM8(MMe)(MMe8)8] eee [MeM8(MMe8)8]+ ee eee (eeee-eeeeeeee) eeeeeeeeeeeeeee eeeeeee.[‌88‌]

Mee eeeeeeee ee eeeeeeeeeeee eeeeee eee eeee ee eeeeee ee eee eeee eeeeeeeeeee ee eee eeeeeeee eeeeeeeee. Meee, ee e eeeee ee eee M—Me eeeeee M—MMe eeeeeeeeeee ee eee Meeeee eeeeeeee ee 8-eeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee eeee eeeeeeee(eeeeee)- ee eeeeeeeee(eeeeee)eeeeeeee, eeee eeeeeeeeeee eee M—Me eeeeeeeeeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeee eeeeee, eeeeeee eee eee ee eeeeee eeeeeeee ee eeeeeeee eeeeee eeeeeeee eeeeeee eee eeeeeeeeeeeeeeeeeeeeeeeee ee eeee 8-eeeeeeeeeeeeee.[‌888‌,‌888‌] Mee eeee-eeeeeeeee eeeeeeee ee 8-eeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee ee eee Meeeee eeeeeeee eee eeee ee eeeeeeeeee ee eee eeeeee ee eeeeeeeee.[‌888‌] Meee, eeeeeeeeeeeeeeeeeeeeee eeeee ee eeeeeeee ee eee M—MMe eeee, eeeeeee eee-eeee-eeeeeeeeeeeeee eeeee ee ee eeeeeeeee eeeeeeee eeeeeee eee M—Me eeee, eeeee eee eeee eeeeeeeeeeee ee eee eeeeeeeee eeeeeee eeeeeeee ee eee eeeeee eeeeeeeee.[‌888‌‌888‌]

Mee eeeeeeeeeeeeeee ee eeeeeeeeeeeeee eeee eee eeeeeeeeeeeeeee eee eeeee eeeeeeeeeee eeee ee α ee8-eeeeee eeeeee eeee eeeeeeeee ee eeeeeeeeeeeee eee eeee eeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeee [MeM8(M)8(M)]+.[‌88‌] Meeeeeeee eee eeee eeeeeeee ee eee eeeeeeee ee ee α-eeeeeeeeeeeeeeeeeeeee[‌888‌] eee α-eeeeeeeeeeeeeeeeeeeeeeeeee.[‌888‌] Meeeeee, eee eee ee eeeeeeee eeeeeeee eee eeeee eee eeeeeee eee eeeeee eeeeeeeeeeeee eeeeeee ee eeeeeeeee ee eeeeeeeeeeeee,[‌88‌] eeeee ee eeeeeeeeee eeee eee eeeeeeeee ee eeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee eeeeeee ee α-eeeeee eeeeeeeeeee eeee eeee eeeeeeeee ee eeeeeee ee eeeeeeeeeeeeeee.[‌88‌,‌88‌,‌888‌,‌888‌]

Mee “eeeeee eeeeee” eee eeee eeeeeeeeeeee eeeeee eee eeeeeeeee eeeeeeee ee eee eeeeeeeeeee eeeeeeeee. Meeeeeeeeee, eeeeee(M) eeeeee eeeeeeee eeee ee eee eeee eeeeeee eeeeee M eeeeeeee eeeeee eee eeeeeeeee eeeeeeee eeee, eeee eeeeeeeeee eee “eeee-eeeeeeeeeee” eeeeeeee ee eee eeeeeeee ee eeee eeeeeee ee eee eeee-eeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeee.[‌888‌] Mee eeeeee ee eeeeeeee eee eeeeeeeeeeeeeeeeee eeee eee eeeeeeeeeeeeeee eeeeeee eee eeee-eeeeeeeeeee ee eeee eeeeeee ee eeee eeeeeeeeeee eee eeeeeeeeeeeeeeeeee, eee eeeeee(M) eeeeee ee e eeee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeee eeee eee eeeeeeeeeeeeeee.

M eee–eeeeee eeeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee eeeeeee eeeee eeee eeeee ee eee eeeeeeee ee eeeeee(M) eeeee. Meee, eee eeeeeeeeeeeeee eeeeeeee ee eeeeeee eeeeeee eeee eeeeeeeeeeeeeeee eee ee eeeeeee eee eeeee eeeeee(M) eeeee eeeeeeeeeeeeee[‌888‌,‌888‌] ee eeeeeeeee eeeeeeeeee.[‌888‌‌888‌] Mee Meeeee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eee eeee eeeeeeee ee eee eeeeeeee ee eeeeee(M).[‌888‌,‌888‌] Meeeeeee, ee eee eeee eeeeeeeee eeee eeeeee(M) eeeeeee eee eeeeeee eeeeeeeee(8) eeeeeeeee eeee ee eee(eee-eeee-eeeeeeeeeeeeee)eeeeeeeee(8) ee eeee e eeeeeeeee eeeeeeeee(M) eeeeeee [MeMe{M(e-Me)8}]8, eeeee eeeee eeeeeeee eeeeee eeeeeeee (eee-eeee-eeeeeeeeeeeeee)eeeeeeeee(8) [Me{M(e-Me)8}][‌888‌] ee eeeee ee eeeeeeeeeee eee eeeeeeeeeee eeeeeeeee eeeeee eeeeeeeee eeeeeeeee(M).[‌888‌]

Meeeeeeeee eeeeeeee eeeeeeeeeeeeeeee eeeee eeeee ee e eeeeeeeee eeeeeeeee, eeeee eeeeeee ee eee eeeeeeeee ee eeee-eeeeeeeeeeee eeeeeeee.[‌888‌‌888‌] Meeeeeeeeee eeeeeee[‌888‌,‌888‌] eeeeeee eee eeeeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeeeeeeee,[‌888‌] eeeeee ee e Meee-eeee eeeeeeee eeeeeeeee eeeeee eeeeeeeee eee α-eeeeeeeeeee ee eee (Meeeee 8). Mee eeeeeeeee eeeeeeeeeeee eeeeeeee eeee eeeeee ee β-eeeeeee eeeeeeeeeee ee eeee 8,8-eeeeeeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeeeee.

Meeeee 8 Meeeeeeee eee eee eeee-Meeeeeeeeeee ee Meeeeeeeeeeeeeee

Meeeeeee ee M eeeeee ee eeeeeeeee eee eeeee ee eee eeeeeeeee eeeeeee eee eeee eeeee eeeee eeee eeeeeeeeee.[‌888‌‌888‌] Meee eeeeeeee eeeeeeee eeeee eeeeeee e eeeeeeeee eeeeeeeeeee ee eeee e eeeeeeeeeee eeee eeeeeeee ee eeeeeeeee eeeeeeee ee e eeeeeeeee M—M eeee.[‌888‌] Meeeeeeeeeee eeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeee eeee–eeee eeeeeeee eeeeeee eeeeeeeee eeeeeeeee(MM) eeeeeeeee eeee eeee eeee eeeeeeee.[‌888‌‌888‌]