Homework Help is Here – Start Your Trial Now!
Science
Chemistry
RO. OR NH4PF6, Pd(TFA)2 (R)-tBuPyOX PhB(OH)2 DCE/H₂O, 60 °C RO OR

RO. OR NH4PF6, Pd(TFA)2 (R)-tBuPyOX PhB(OH)2 DCE/H₂O, 60 °C RO OR

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
See similar textbooks
icon
Related questions
Question

Propose a mechanism for the following reaction.

Subjected to asymmetric 1,4-addition

**Transcription:** This chemical reaction depicts the transformation of a naphthoquinone derivative into a substituted product using a palladium-catalyzed process. Below are the details of the reaction conditions and components: **Reactants and Catalysts:** - **Chemical Starting Material:** A naphthoquinone derivative, labeled with R groups attached to the oxygen atoms. - **Catalysts and Reagents:** - \( \text{NH}_4\text{PF}_6 \) - \( \text{Pd(TFA)}_2 \) (Palladium(II) trifluoroacetate) - \( (\text{R})\text{-tBuPyOX} \) (chiral ligand) - \( \text{PhB(OH)}_2 \) (phenylboronic acid) **Solvent and Conditions:** - Solvent: Dichloroethane/Water (DCE/\(\text{H}_2\text{O}\)) - Temperature: \( 60^\circ \text{C} \) **Product:** - The product features a benzene ring (highlighted in red) added to the original naphthoquinone structure through a palladium-catalyzed arylation reaction. The benzene ring is attached via a newly formed bond to the naphthoquinone moiety. This reaction is an example of a palladium-catalyzed C-H activation and arylation, which is useful for introducing aromatic groups into complex molecular scaffolds in organic synthesis.
Transcribed Image Text:**Transcription:** This chemical reaction depicts the transformation of a naphthoquinone derivative into a substituted product using a palladium-catalyzed process. Below are the details of the reaction conditions and components: **Reactants and Catalysts:** - **Chemical Starting Material:** A naphthoquinone derivative, labeled with R groups attached to the oxygen atoms. - **Catalysts and Reagents:** - \( \text{NH}_4\text{PF}_6 \) - \( \text{Pd(TFA)}_2 \) (Palladium(II) trifluoroacetate) - \( (\text{R})\text{-tBuPyOX} \) (chiral ligand) - \( \text{PhB(OH)}_2 \) (phenylboronic acid) **Solvent and Conditions:** - Solvent: Dichloroethane/Water (DCE/\(\text{H}_2\text{O}\)) - Temperature: \( 60^\circ \text{C} \) **Product:** - The product features a benzene ring (highlighted in red) added to the original naphthoquinone structure through a palladium-catalyzed arylation reaction. The benzene ring is attached via a newly formed bond to the naphthoquinone moiety. This reaction is an example of a palladium-catalyzed C-H activation and arylation, which is useful for introducing aromatic groups into complex molecular scaffolds in organic synthesis.
Expert Solution
steps

Step by step

Solved in 6 steps with 4 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Phase Diagrams
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.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS