2. When the following Negishi cross-coupling reaction was attempted, two different products were observed. (A) Draw a plausible catalytic cycle that explains the formation of the desired product. Label all mechanistic sticks. [Pd] can be used as the active catalyst. (B) Suggest how the undesired side-product may have formed. Hint: alkyl-Pd species are not particularly stable. Br ZnCl [Pd] catalyst desired product undesired side-product
2. When the following Negishi cross-coupling reaction was attempted, two different products were observed. (A) Draw a plausible catalytic cycle that explains the formation of the desired product. Label all mechanistic sticks. [Pd] can be used as the active catalyst. (B) Suggest how the undesired side-product may have formed. Hint: alkyl-Pd species are not particularly stable. Br ZnCl [Pd] catalyst desired product undesired side-product
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![2. When the following Negishi cross-coupling reaction was attempted, two different products
were observed. (A) Draw a plausible catalytic cycle that explains the formation of the
desired product. Label all mechanistic sticks. [Pd] can be used as the active catalyst.
(B) Suggest how the undesired side-product may have formed. Hint: alkyl-Pd species
are not particularly stable.
Br
+
ZnCl
[Pd] catalyst
´N´
desired
product
undesired
side-product](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F0b07e2d2-f4aa-4da8-9546-080d6b9a3349%2Fc0a7f2e3-0cab-4161-8b61-91bd4a8166d7%2F6vz52mp_processed.png&w=3840&q=75)
Transcribed Image Text:2. When the following Negishi cross-coupling reaction was attempted, two different products
were observed. (A) Draw a plausible catalytic cycle that explains the formation of the
desired product. Label all mechanistic sticks. [Pd] can be used as the active catalyst.
(B) Suggest how the undesired side-product may have formed. Hint: alkyl-Pd species
are not particularly stable.
Br
+
ZnCl
[Pd] catalyst
´N´
desired
product
undesired
side-product
Expert Solution
Step 1: Introduction to The Negishi cross-coupling reaction
The general reaction mechanism involves oxidative addition of the palladium catalyst to the organozinc compound, followed by transmetallation with the organic halide and reductive elimination to form the C-C bond. The overall process allows for the controlled construction of complex organic molecules by selectively coupling different organic groups.
The Negishi cross-coupling reaction is valuable in synthetic chemistry for the creation of various pharmaceuticals, agrochemicals, and other organic compounds. It provides a versatile tool for chemists to build complex molecular structures efficiently and selectively.
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