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Palladium-Catalyzed Cross Coupling reactions are new methods of synthesizing C-C

ID: 524118 • Letter: P

Question

Palladium-Catalyzed Cross Coupling reactions are new methods of synthesizing C-C bonds. The products that result are often good candidates for new drugs. There are four palladium-catalyzed cross-coupling reactions that you should know. The 2010 Nobel Prize in Chemistry was awarded to Negishi, Sukuzi and Heck for their work. (Stille died in a plane crash in 1989.) Organotin reagent (Stille) Organozinc reagent Negishi) Organoboron reagent (Suzuki) Alkene (Heck) Draw product of the following Negishi cross-coupling reaction: CH3-CH_2-Zn-Cl + O_2N-CH_2-CH_2-Br Pd(PPh_3)_4 rightarrow Draw the product of the following Heck cross-coupling reaction: Br-CH_2-CH = CH_2 + CH_2 = CH - CH_2 - CH_3 Pd(OAc)_2, Ph_5P rightarrow Base

Explanation / Answer

9) Answer:

Negishi cross-coupling product:

CH3-CH2-CH2-CH2-NO2

10) Answer:

Heck-cross coupling product:

CH2=CH-CH2-CH2-CH2-CH2-CH3