Stereoselective Palladium-Catalyzed C(sp3)–H Mono-Arylation of Piperidines and Tetrahydropyrans with a C(4) Directing Group
DOI: 10.14469/hpc/10148 Metadata
Created: 2022-02-15 12:46
Last modified: 2022-03-07 18:06
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Description
We describe an efficient and highly stereoselective palladium-catalyzed methodology for the C(3) mono-cis functionalization of unbiased piperidines and tetrahydropyrans bearing a C(4) aminoquinoline directing group. Significantly lower reaction temperatures (≤50 °C) are employed compared to other reported heterocycle C(sp3)–H functionalization reactions and divergent directing group removal is demonstrated, with valuable fragments being accessed in only 3-4 synthetic steps from inexpensive commercial materials.
Files
| Filename | Size | Type | Description |
|---|---|---|---|
| Piperidine and Tetrahydropyran Amide Substrates 1, S27-29, 6-8 and 12.zip | 49MB | application/zip | Piperidine and Tetrahydropyran Amide Substrates 1, S27-29, 6-8 and 12 |
| Piperidine and Tetrahydropyran Amide Substrates 1, S27-29, 6-8 and 12.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for Piperidine and Tetrahydropyran Amide Substrates 1, S27-29, 6-8 and 12.zip |
| NBoc Piperidine Arylation Products 2a, 3a, 4a, 5a.zip | 99MB | application/zip | Characterization of N-Boc Piperidine Arylation Products 2a, 3a, 4a, 5a |
| NBoc Piperidine Arylation Products 2a, 3a, 4a, 5a.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for NBoc Piperidine Arylation Products 2a, 3a, 4a, 5a.zip |
| NBoc Piperidine S34.zip | 26MB | application/zip | Characterization of N-Boc Piperidine Arylation Product S34 |
| NBoc Piperidine S34.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for NBoc Piperidine S34.zip |
| Piperidine C-H Arylation Scope of N Protecting Groups (9a-11a).zip | 39MB | application/zip | Piperidine C–H Arylation: Scope of N-Protecting Groups (9a-11a) |
| Piperidine C-H Arylation Scope of N Protecting Groups (9a-11a).mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for Piperidine C-H Arylation Scope of N Protecting Groups (9a-11a).zip |
| Piperidine C-H Arylation Scope of Aryl Iodides (2a-2u and S30-32).zip | 491MB | application/zip | Piperidine C–H Arylation: Scope of Aryl Iodides (2a-2u and S30-32) |
| Piperidine C-H Arylation Scope of Aryl Iodides (2a-2u and S30-32).mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for Piperidine C-H Arylation Scope of Aryl Iodides (2a-2u and S30-32).zip |
| One-pot Arylation Epimerisation trans-disubstituted piperidines 3a and 18.zip | 33MB | application/zip | One-pot Arylation Epimerization: 3,4-trans-Disubstituted Piperidines (3a, 18) |
| One-pot Arylation Epimerisation trans-disubstituted piperidines 3a and 18.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for One-pot Arylation Epimerisation trans-disubstituted piperidines 3a and 18.zip |
| Tetrahydropyran C-H Arylation Scope of Aryl Iodides (13a-13j).zip | 53MB | application/zip | Tetrahydropyran C–H Arylation: Scope of Aryl Iodides (13a-13j) |
| Tetrahydropyran C-H Arylation Scope of Aryl Iodides (13a-13j).mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for Tetrahydropyran C-H Arylation Scope of Aryl Iodides (13a-13j).zip |
| Diarylation Studies on 2c (14, 15, 16, 17).zip | 118MB | application/zip | Diarylation Studies on N-Boc cis-Arylated Piperidine 2c |
| Diarylation Studies on 2c (14, 15, 16, 17).mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for Diarylation Studies on 2c (14, 15, 16, 17).zip |
| Removal of AQ Directing Group (20-22 and S33).zip | 96MB | application/zip | Removal of AQ Directing Group (20-22 and S33) |
| Removal of AQ Directing Group (20-22 and S33).mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for Removal of AQ Directing Group (20-22 and S33).zip |
| NBoc Deprotection Fragment Synthesis (23-26).zip | 34MB | application/zip | N-Boc Deprotection: Fragment Synthesis (23-26) |
| NBoc Deprotection Fragment Synthesis (23-26).mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for NBoc Deprotection Fragment Synthesis (23-26).zip |