6. During alkylation of bromobenzene with sec-butylmagnesium chloride, researchers at Johnson-Mattheyfound that the ratio of A to B was sensitive to the bite angle of the chelating diphosphine supporting thePd catalyst (see scheme below).Mereductive eliminationproduct (desired)MePd catalystseo-BuMgClD-hydride elimination/Mesomerization productrt(undesired)competing reaction pathways of Pd() intermediates95%43%Ph99Pd Me1 h919PdFe24 h-PPh2Me0%19%Me(a) Provide mechanisms for formation of both A and B, starting from bromobenzene. Please nameeach 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 PMDELL

Mechanisms for formation of both A and B is given below

(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

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.36P

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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

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