Regioselective Benzylic C–H Alumination and Further Functionalization of 2‑Alkylpyridines by Yttrium Catalyst
The regioselective benzylic C–H alumination of various symmetrical and nonsymmetrical 2,6-alkylpyridines catalyzed by a half-sandwich yttrium complex has been developed. The resulting alkylaluminum species bearing a pyridyl ring moiety can be transformed to the corresponding alcohols by oxidation. M...
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| Published in | ACS catalysis Vol. 12; no. 21; pp. 13792 - 13804 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
American Chemical Society
04.11.2022
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| Subjects | |
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| Abstract | The regioselective benzylic C–H alumination of various symmetrical and nonsymmetrical 2,6-alkylpyridines catalyzed by a half-sandwich yttrium complex has been developed. The resulting alkylaluminum species bearing a pyridyl ring moiety can be transformed to the corresponding alcohols by oxidation. Moreover, the Cu-catalyzed allylation and benzylation and Pd-catalyzed arylation reactions can be applied to the resulting alkylaluminum species, giving the corresponding α-mono-allylated, α-mono-benzylated, and α-mono-arylated 2-alkylpyridine derivatives, respectively, in good to high yields. Unsymmetrically substituted 2,6-dialkylpyridines can be synthesized from simple symmetrical substrates by repeating such C–H alumination/C–C bond formation processes. Because of the high regioselectivity of the present C–H alumination and the subsequent C–C bond formation, this protocol may serve as a desirable method for the synthesis of nonsymmetrically-2,6-disubstituted pyridine derivatives. |
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| AbstractList | The regioselective benzylic C–H alumination of various symmetrical and nonsymmetrical 2,6-alkylpyridines catalyzed by a half-sandwich yttrium complex has been developed. The resulting alkylaluminum species bearing a pyridyl ring moiety can be transformed to the corresponding alcohols by oxidation. Moreover, the Cu-catalyzed allylation and benzylation and Pd-catalyzed arylation reactions can be applied to the resulting alkylaluminum species, giving the corresponding α-mono-allylated, α-mono-benzylated, and α-mono-arylated 2-alkylpyridine derivatives, respectively, in good to high yields. Unsymmetrically substituted 2,6-dialkylpyridines can be synthesized from simple symmetrical substrates by repeating such C–H alumination/C–C bond formation processes. Because of the high regioselectivity of the present C–H alumination and the subsequent C–C bond formation, this protocol may serve as a desirable method for the synthesis of nonsymmetrically-2,6-disubstituted pyridine derivatives. |
| Author | Hou, Zhaomin Takimoto, Masanori Liu, Mingyu Nishiura, Masayoshi |
| AuthorAffiliation | Advanced Catalysis Research Group RIKEN Center for Sustainable Resource Science Nankai University College of Chemistry Organometallic Chemistry Laboratory RIKEN Cluster for Pioneering Research |
| AuthorAffiliation_xml | – name: RIKEN Cluster for Pioneering Research – name: Organometallic Chemistry Laboratory – name: Advanced Catalysis Research Group – name: RIKEN Center for Sustainable Resource Science – name: College of Chemistry – name: Nankai University |
| Author_xml | – sequence: 1 givenname: Masanori orcidid: 0000-0002-2575-3303 surname: Takimoto fullname: Takimoto, Masanori email: mtakimoto@riken.jp organization: RIKEN Center for Sustainable Resource Science – sequence: 2 givenname: Mingyu orcidid: 0000-0003-4649-7393 surname: Liu fullname: Liu, Mingyu organization: Nankai University – sequence: 3 givenname: Masayoshi orcidid: 0000-0003-2748-9814 surname: Nishiura fullname: Nishiura, Masayoshi organization: RIKEN Center for Sustainable Resource Science – sequence: 4 givenname: Zhaomin orcidid: 0000-0003-2841-5120 surname: Hou fullname: Hou, Zhaomin email: houz@riken.jp organization: RIKEN Center for Sustainable Resource Science |
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| CitedBy_id | crossref_primary_10_1021_jacs_4c09067 crossref_primary_10_1039_D4OB00268G crossref_primary_10_1021_jacs_4c02144 crossref_primary_10_1007_s11426_023_1588_8 crossref_primary_10_1021_jacs_4c17210 crossref_primary_10_1038_s41467_025_56905_8 crossref_primary_10_1002_ange_202318203 crossref_primary_10_1021_jacs_3c06482 crossref_primary_10_1016_j_tet_2023_133323 crossref_primary_10_1002_anie_202318203 |
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| Keywords | organoaluminums cross-coupling reaction pyridines C−H activation rare-earth metal catalysts |
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| Snippet | The regioselective benzylic C–H alumination of various symmetrical and nonsymmetrical 2,6-alkylpyridines catalyzed by a half-sandwich yttrium complex has been... |
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| StartPage | 13792 |
| Title | Regioselective Benzylic C–H Alumination and Further Functionalization of 2‑Alkylpyridines by Yttrium Catalyst |
| URI | http://dx.doi.org/10.1021/acscatal.2c04396 |
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