(a) Provide mechanisms for formation of both A and B, starting from bromobenzene. Please name each elementary step (e.g. oxidative addition, transmetalation, etc.). (b) Why is catalyst 1 more efficient at forming A and suppressing B than catalyst 2?
(a) Provide mechanisms for formation of both A and B, starting from bromobenzene. Please name each elementary step (e.g. oxidative addition, transmetalation, etc.). (b) Why is catalyst 1 more efficient at forming A and suppressing B than catalyst 2?
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.58P
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Question
![6. During alkylation of bromobenzene with sec-butylmagnesium chloride, researchers at Johnson-Matthey
found that the ratio of A to B was sensitive to the bite angle of the chelating diphosphine supporting the
Pd catalyst (see scheme below).
Me
reductive elimination
product (desired)
Me
Pd catalyst
seo-BuMgCl
D-hydride elimination/
Me
somerization product
rt
(undesired)
competing reaction pathways of Pd() intermediates
95%
43%
Ph
99
Pd Me
1 h
919
Pd
Fe
24 h
-PPh2
Me
0%
19%
Me
(a) Provide mechanisms for formation of both A and B, starting from bromobenzene. Please name
each elementary step (e.g. oxidative addition, transmetalation, etc.).
(b) Why is catalyst 1 more efficient at forming A and suppressing B than catalyst 2?
1241 PM
DELL](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd36e81a8-5893-4cd3-832d-85f074e14873%2Faa2a44de-b698-4f27-8db6-e41c6584feec%2Fh2ftbej_processed.jpeg&w=3840&q=75)
Transcribed Image Text:6. During alkylation of bromobenzene with sec-butylmagnesium chloride, researchers at Johnson-Matthey
found that the ratio of A to B was sensitive to the bite angle of the chelating diphosphine supporting the
Pd catalyst (see scheme below).
Me
reductive elimination
product (desired)
Me
Pd catalyst
seo-BuMgCl
D-hydride elimination/
Me
somerization product
rt
(undesired)
competing reaction pathways of Pd() intermediates
95%
43%
Ph
99
Pd Me
1 h
919
Pd
Fe
24 h
-PPh2
Me
0%
19%
Me
(a) Provide mechanisms for formation of both A and B, starting from bromobenzene. Please name
each elementary step (e.g. oxidative addition, transmetalation, etc.).
(b) Why is catalyst 1 more efficient at forming A and suppressing B than catalyst 2?
1241 PM
DELL
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