Intramolecular Palladium(II)/(IV) Catalysed C(sp3)–H Arylation of Tertiary Aldehydes using a Transient Directing Group
DOI: 10.14469/hpc/5614 Metadata
Created: 2019-05-10 13:31
Last modified: 2019-12-18 09:14
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: James A. Bull
Description
Palladium catalysed β-C(sp3)–H activation of tertiary aldehydes using a transient imine directing group enables intramolecular arylation to form substituted indane-aldehydes. A simple amine bearing a methyl ether (2-methoxyethan-1-amine) was the optimal TDG to promote C–H activation and reaction with a proximal C–Br bond. Various substituted derivatives are prepared and the aldehyde functionality is exploited to derivatise the products. Preliminary mechanistic studies identify a reversible C–H activation, product inhibition and suggest that oxidative addition is the turnover limiting step.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/5618 | 4. Mechanistic experiments |
| 10.14469/hpc/5616 | 2. Products 4 and 18-25 |
| 10.14469/hpc/5615 | 1. Substrates 1-3 and 5-16 |
| 10.14469/hpc/5617 | 3. Derivatives 27-30 |