Account for the formation of the product and for the cis stereochemistry of its ring junc- tion. (The function of silver carbonate is to enhance the rate of reaction.) COOME COOME Pd(OAc)g, PPh, Ag,COg, CH,CN H 86%

Account for the formation of the product and for the cis stereochemistry of its ring junc- tion. (The function of silver carbonate is to enhance the rate of reaction.) COOME COOME Pd(OAc)g, PPh, Ag,COg, CH,CN H 86%

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 24.13P

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Question

Account for the formation of the product and for the cis stereochemistry of its ring junc-
tion. (The function of silver carbonate is to enhance the rate of reaction.)
COOME
COOME
Pd(OAc)g, PPh,
Ag,COg, CH,CN
H
86%

Expert Solution

Step 1

$T h e o x i d a t i v e a d d i t i o n o f a r y l h a l i d e f o r m s a n o r g a n o p a l l a d i u m c o m p o u n d w i t h P d (P P h 3) 2 .$

Step 2

$T h e s y n a d d i t i o n o f t h e b e n z e n e r i n g a n d P d (P P h 3) 2 I o f t h i s c o m p l e x t o t h e a l k e n e g i v e s a n o r g a n o p a l l a d i u m i n t e r m e d i a t e (B) .$

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