Answer ALL parts a) - c). In the following reaction sequence, the synthesis of compound 4 is achieved. Ts HN Ph Grubbs catalyst A Ar-Br TFA B Pd:(dba)3 P(t-Bu)3 Ph N. Ph base 3 4 b) Compound A undergoes a Heck reaction to give product B, which is not isolated but directly reacted with trifluoroacetic acid (TFA) to give the heterocyclic compound 3. Draw the curly arrow mechanism from A to B. Which type of reactions are involved in the conversion from B to 3? Suggest a mechanism for the conversion from B to 3. Draw the structure of the required arylbromide (Ar-Br) which is needed for the synthesis of 3. i1) iv)

Answer ALL parts a) - c). In the following reaction sequence, the synthesis of compound 4 is achieved. Ts HN Ph Grubbs catalyst A Ar-Br TFA B Pd:(dba)3 P(t-Bu)3 Ph N. Ph base 3 4 b) Compound A undergoes a Heck reaction to give product B, which is not isolated but directly reacted with trifluoroacetic acid (TFA) to give the heterocyclic compound 3. Draw the curly arrow mechanism from A to B. Which type of reactions are involved in the conversion from B to 3? Suggest a mechanism for the conversion from B to 3. Draw the structure of the required arylbromide (Ar-Br) which is needed for the synthesis of 3. i1) iv)

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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