The Stille coupling reaction is another metal-catalyzed reaction that is a great way to form carbon-carbon bonds. What makes the Stille coupling unique is that it is a carbonylative reaction, meaning CO is inserted into the compound to make a carbonyl group. The mechanism involves oxidative addition, coordination, insertion, transmetallation, and reductive elimination. Suggest a mechanism for the following Stille coupling. OTf Me Si SnBu3 cat. Pd(PH3)4 LICI, 1.1 atm CO C12H20OSI

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 42MP
icon
Related questions
Question
The Stille coupling reaction is another metal-catalyzed reaction that is a great
way to form carbon-carbon bonds. What makes the Stille coupling unique is that it
is a carbonylative reaction, meaning CO is inserted into the compound to make a
carbonyl group. The mechanism involves oxidative addition, coordination,
insertion, transmetallation, and reductive elimination. Suggest a mechanism for the
following Stille coupling.
OTf
Me Si
SnBu3
cat. Pd(PH3)4
LICI, 1.1 atm CO
C12H20OSI
Transcribed Image Text:The Stille coupling reaction is another metal-catalyzed reaction that is a great way to form carbon-carbon bonds. What makes the Stille coupling unique is that it is a carbonylative reaction, meaning CO is inserted into the compound to make a carbonyl group. The mechanism involves oxidative addition, coordination, insertion, transmetallation, and reductive elimination. Suggest a mechanism for the following Stille coupling. OTf Me Si SnBu3 cat. Pd(PH3)4 LICI, 1.1 atm CO C12H20OSI
Expert Solution
steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Selection Rules for Pericyclic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning