Migita—Stille cross-coupling

Owing to the careful and comprehensive work of Stille and, more recently, of Amadore and Jutand [84], the Migita-Stille cross-coupling enjoys the position of the most mechanistically understood of the named cross-coupling processes [23a]. Nevertheless, there is no ideal catalytic system, and that each reaction requires... 

Scheme 14.22 The DoM-Migita-Stille cross-coupling nexus in the synthesis of antimitotic rhazinilam 98 mimics [134].

Scheme 14.35 The DoM-Migita-Stille cross-coupling-DreM strategy. Synthesis of kinafluorenone 179 [152].

In another approach to isoschumanniophytine 201 (Scheme 14.40) [156], a Migita-Stille cross-coupling of tributylstannylpyridine 202 with the DoM-derived iodo O-carbamate 204 gives the azabiaryl 206 in fair yields. Better results are obtained when 4-bromopyridine hydrochloride 203 is combined with the... 

Scheme 14.40 The DoM-Suzuki-Miyaura and Migita-Stille cross-coupling/remote anionic Fries rearrangement. Synthesis of isoschumanniophytine 201 (156).

DoM-Migita-Stille Cross-Coupling for the Preparation of3,3"-Dimethoxy-2,2 5 2"-terthiophene 228 (Scheme 14.44)... 

For similar halopyridine DoM tactics to manipulate Suzuki-Miyaura and Migita-Stille cross-coupling reactivity and nucleophilic heteroaromatic substitution to effect indole ring closure, see the reports on the synthesis of lavendamycin analogues ... 

Scheme 3-215. General catalytic cycle of Kosugi-Migita-Stille cross-coupling.

Similarly, the Migita-Kosugi-Stille cross-coupling reaction (Equation (115)) is important in organic synthesis and has IS 190 302 303, 1... 

STILLE CROSS-COUPLING (MIGITA-KOSUGI-STILLE COUPLING)... 

The first paper that demonstrated the feasibility of a palladium-catalyzed amination was a report by T. Migita and co-workers.6 They demonstrated that a tri-ortho-tolyl phosphine palladium chloride catalyst will catalyze the cross-coupling of N,N-diethylamino-tributyltin with bromobenzene. The process can be thought of as an amino-Stille cross-coupling. 

Cyclopentadienylstannanes can be used in the Migita-Kosugi-Stille reaction with organic iodides, RI, to give the cross-coupled product Cp-R, for example, Equation (117).310... 

Cross-coupling reactions 5-alkenylboron boron compounds, 9, 208 with alkenylpalladium(II) complexes, 8, 280 5-alkylboron boron, 9, 206 in alkyne C-H activations, 10, 157 5-alkynylboron compounds, 9, 212 5-allylboron compounds, 9, 212 allystannanes, 3, 840 for aryl and alkenyl ethers via copper catalysts, 10, 650 via palladium catalysts, 10, 654 5-arylboron boron compounds, 9, 208 with bis(alkoxide)titanium alkyne complexes, 4, 276 carbonyls and imines, 11, 66 in catalytic C-F activation, 1, 737, 1, 748 for C-C bond formation Cadiot-Chodkiewicz reaction, 11, 19 Hiyama reaction, 11, 23 Kumada-Tamao-Corriu reaction, 11, 20 via Migita-Kosugi-Stille reaction, 11, 12 Negishi coupling, 11, 27 overview, 11, 1-37 via Suzuki-Miyaura reaction, 11, 2 terminal alkyne reactions, 11, 15 for C-H activation, 10, 116-117 for C-N bonds via amination, 10, 706 diborons, 9, 167... 

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