by Liang Zhang, Gabriel J. Lovinger, Emma K. Edelstein, Adam A

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Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement by Liang Zhang, Gabriel J. Lovinger, Emma K. Edelstein, Adam A. Szymaniak, Matteo P. Chierchia, and James P. Morken Science Volume 351(6268):70-74 January 1, 2016 Published by AAAS

Fig. 1 Metal-induced metallate shift as a strategy for catalytic reaction design. Metal-induced metallate shift as a strategy for catalytic reaction design. (A) The catalytic conjunctive cross-coupling process. (B) Common metallate shift to saturated carbon centers requires a leaving group. L, ligand. (C) Metallate shift to unsaturated carbons is often activated by addition of an external electrophile. M, metal; E, electrophile. (D) A metallate shift promoted by a metal complex can serve as an alternative to a transmetallation process. (E) Proposed catalytic cycle for conjunctive cross-coupling. Ar, aryl group. Liang Zhang et al. Science 2016;351:70-74 Published by AAAS

Fig. 2 Scope of the catalytic conjunctive cross-coupling reaction starting from vinyl boronic esters. Scope of the catalytic conjunctive cross-coupling reaction starting from vinyl boronic esters. Yields represent isolated yield of purified material and are an average of two experiments. The absolute configuration was determined by anomalous dispersion x-ray and by chromatographic comparison to known compounds. *VinylB(neo) was replaced with vinylB(pin); †reaction conducted at 80°C. er was determined by chiral supercritical fluid chromatography. OAc, acetate; Me, methyl group; Ph, phenyl group; OTf, trifluoromethanesulfonate; OTBS, tert-butyldimethylsiloxy. Liang Zhang et al. Science 2016;351:70-74 Published by AAAS

Fig. 3 Scope of the catalytic conjunctive cross-coupling reaction starting from alkyl or aryl boronic esters. Scope of the catalytic conjunctive cross-coupling reaction starting from alkyl or aryl boronic esters. Yields represent isolated yield of purified material and are an average of two experiments. Cy, cyclohexyl group. Liang Zhang et al. Science 2016;351:70-74 Published by AAAS

Fig. 4 Synthesis and mechanistic studies. Synthesis and mechanistic studies. (A) Synthesis of combretastatin by conjunctive cross-coupling. (B) The stereochemical course of metal-induced metallate rearrangement. dr, diastereomeric ratio. Liang Zhang et al. Science 2016;351:70-74 Published by AAAS