Abstract
The story of C−C bond formation includes several reactions, and surely Suzuki‐Miyaura is among the most outstanding ones. Herein, a brief historical overview of insights regarding the reaction mechanism is provided. In particular, the formation of the catalytically active species is probably the main concern, thus the preactivation is in competition with, or even assumes the role of the rate determining step (rds) of the overall reaction. Computational chemistry is key in identifying the rds and thus leading to milder conditions on an experimental level by means of predictive catalysis.
Highlights
Suzuki-Miyaura cross-coupling reactions follow a well-defined catalytic cycle based on three steps[103] (Scheme 9): i) oxidative addition of the organic halide or other electrophiles to the palladium(0) complex to give R1-PdII-X; ii) transmetalation
Knowing that catalysis is the way to escape stoichiometric reactions and at the same time to render reactions faster, the Suzuki-Miyaura cross coupling reaction is generally catalyzed by taking palladium as a reference metal
The rate determining step of the overall reaction pathway is not placed in the catalytic pathway but identified as one of the steps included in induction period
Summary
Carbon-carbon bond formation reactions are essential for the development of bioactive molecules, agrochemicals and drugs. They are used to construct new organic materials with innovative electronic, optical or mechanical properties in the field of nanotechnology.[1] these types of reactions, known as cross-coupling reactions, have been some of the greatest breakthroughs in the fields of organic/ organometallic synthesis since the discovery of catalysis.[2] That is why over the last half century, CÀ C bond formation reactions have been extensively studied and new methodologies have been developed using transition metals to mediate reactions in a controlled and selective manner, under mild conditions. CÀ C cross-coupling reactions are defined as carbon-carbon bond formation reactions between an organic electrophile (R1X) and an organometallic nucleophile (R2-m) in the presence of a metal catalyst [M] (Scheme 1). The Negishi reaction utilizes organozinc reagents, the Stille reaction utilizes organotin reagents, the Suzuki-Miyaura reaction utilizes organoboron reagents, etc
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