3BL-Lecture08 - Welcome to Chemistry 3BL Lecture 8 David...

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Welcome to Chemistry 3BL Lecture 8 David Rabuka
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Suzuki Lab Reflections • Questions for the Suzuki lab are posted on the Chem 3BL bspace site. • Let’s examine the theory in more detail.
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The Suzuki Reaction Important Notices for Your Lab Report: • Include an analysis of the 1 H-NMR and 13 C- NMR spectrum of the product of the Suzuki reaction, as directed in the posted questions. • The analysis need not be exhaustive. • Also, follow the directions for writing the discussion section of the lab report: comment on the method used to establish the identity and purity of your product, discuss the role of each reactant/starting material in the cycle, and discuss the merits of the Suzuki reaction.
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Green Chemistry: Avoid using heavy metals and other chemicals that can have long term toxic effects. Choose water and other friendlier chemicals whenever possible. • If the use of toxic chemicals is necessary, develop reactions that can use them in catalytic amounts. • Reduce the amounts of “waste” that are produced by doing things on small scale when possible. • Minimize the use of flammable, explosive, and highly reactive chemicals.
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Redesign the Friedel-Crafts reaction to be green List factors from the Friedel-Crafts reaction that might not be friendly to the environment. • Are there environmentally friendly alternatives for these factors that would help us redesign the reaction?
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The Suzuki Reaction: Friedel-Crafts’ “Green” Cousin Br O B HO OH Pd(OAc) 2 (catalyst) Bu 4 NBr K 2 CO 3 H 2 O (solvent) + O • Used Pd, but in catalytic amounts. • Uses water as a solvent rather than organic solvent. • No toxic/highly reactive/flammable/explosive by-products. • As always you performed the reaction on a microscale.
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Suzuki Mechanism Pd(II)(OAc) 2 Pd(0) reduced Br O Pd(II) O Br OXIDATIVE ADDITION Pd inserts in C-Br bond (like Grignard) HO - K + (II) Pd O OH K + Br - hydroxide exchange for bromide K 2 CO 3 + H 2 O Pd(II) O OH B HO HO OH B HO HO OH B HO HO HO - hydroxide exchange for phenyl O REDUCTIVE ELIMNATION C-C bond forms, Pd(II) reduced to Pd(0)
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3BL-Lecture08 - Welcome to Chemistry 3BL Lecture 8 David...

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