(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?

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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
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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