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3.6.13.1.2.1 Gold-Catalyzed Suzuki Reactions

DOI: 10.1055/sos-SD-103-00038

Hopkinson, M. N.; Gouverneur, V.Science of Synthesis Knowledge Updates, (20112108.

The Suzuki reaction between aryl halides and arylboronic acids is the most widely applied method for the construction of biaryls, which are important components in natural products, pharmaceuticals, agrochemicals, and materials. An efficient Suzuki reaction performed with catalytic amounts of gold(I) has been developed by Corma and co-workers.[‌47‌‌50‌] Aryl iodides react with arylboronic acids to afford the corresponding cross-coupled products with high conversions when treated with gold(I) complexes bearing Schiff base[‌47‌,‌49‌,‌50‌] or N-heterocyclic carbene ligands, e.g. 17 and 18, respectively (Scheme 9).[‌48‌,‌49‌] Notably, the process is also successful using commercially available chloro(tri­phenylphosphine)gold(I). Heterogenized gold(I) complexes[‌48‌‌50‌] and gold nanoparticles[‌51‌] are also suitable catalysts for this transformation. Conversely, gold(III) catalysts do not lead to cross-coupled products, instead delivering C2-symmetric biaryls resulting from homocoupling of the boronic acid.[‌52‌,‌53‌]

Meeeee 8 Meee(M)-Meeeeeeee Meeeee Meeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 8

Meeeeeee Meeeeeeeee (%) Mee
[88•(MeMMe8)8]Me 88 [‌88‌]
88•MeMe 88 [‌88‌]
MeMe(MMe8) 88 [‌88‌]

References


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