TY - JOUR
T1 - A Zinc Catalyzed C(sp3)−C(sp2) Suzuki–Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates
AU - Procter, Richard J.
AU - Dunsford, Jay J.
AU - Rushworth, Philip J.
AU - Hulcoop, David G.
AU - Layfield, Richard A.
AU - Ingleson, Michael J.
N1 - Output was published before staff member joined UoE. Proxy DoA used (1 month prior to publish date) to enable OA calculation.
PY - 2017/9/27
Y1 - 2017/9/27
N2 - The Suzuki–Miyaura (SM) reaction is one of the most important methods for C−C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr2, in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.
AB - The Suzuki–Miyaura (SM) reaction is one of the most important methods for C−C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr2, in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.
KW - alkylation
KW - boron
KW - cross-coupling
KW - transmetallation
KW - zincate
UR - http://www.scopus.com/inward/record.url?scp=85031681448&partnerID=8YFLogxK
U2 - 10.1002/chem.201704170
DO - 10.1002/chem.201704170
M3 - Article
AN - SCOPUS:85031681448
SN - 0947-6539
VL - 23
SP - 15889
EP - 15893
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 63
ER -