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Direct Arylation

Direct Arylation. Speaker: Chien -An Chen Teacher: Guey -Sheng Liou. Important bi(hetero)aryls. Direct Arylation V.S. Traditional Cross-Coupling. Define of direct arylation : Through cleavage of C-H bond. Advantage of direct arylation : Without metallic halides by-product

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Direct Arylation

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  1. Direct Arylation Speaker: Chien-An Chen Teacher: Guey-Sheng Liou

  2. Important bi(hetero)aryls

  3. Direct Arylation V.S. Traditional Cross-Coupling Define of direct arylation: Through cleavage of C-H bond Advantage of direct arylation: Without metallic halides by-product →good for enviorment Reduce the synthetic operations →economical

  4. Category of Direct Arylation

  5. Direct Arylation with Organometallic Reagents (Rh-cat.)

  6. Direct Arylation with Organometallic Reagents (Pd-cat.)

  7. Direct Arylation with Organometallic Reagents (Ru-cat.)

  8. DehydrogenativeArylation

  9. Direct Arylation with (Pseudo)Halides (Pd-cat.)

  10. Direct Arylation on LBG polymer UllrichScherf et al. , ACS Macro Lett. 2012, 1, 465−468

  11. Direct Arylation on LBG polymer TakakiKanbara et al. , ACS Macro Lett. 2012, 1, 67−70

  12. Direct Arylation on LBG polymer • Disadvantage: The critical factor of direct arylation polymerization is regioselectivity. Example: Solution method: Use protecting group, methyl, to protect 3-position of thiophene. Example: The two hydrogen atoms are also reactive Cross-linked polymer

  13. Conclusion • Until very recently, the majority of catalytic direct arylationshave been accomplished with palladium, rhodium, or ruthenium catalysts. However, less-expensive copper, iron, and nickel compounds have been shown. • The use of atom-economical terminal oxidants and achieving regioselectivity in intermolecular arylations remain significant challenges.

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