Ligand-Free RuCl3-Catalyzed Alkylation of Methylazaarenes with Alcohols

Tong Yu Feng, Hong Xi Li, David James Young, Jian Ping Lang

Research output: Contribution to journalArticleResearchpeer-review

Abstract

RuCl3 efficiently catalyzes the alkylation of methylquinolines, methylpyridines, 2-methyl-benzooxazoles, and 2-methyl-quinoxalines with alkyl- or aryl-alcohols as alkylating agents. This synthetically useful and atom economical transformation does not require additional ligands. The mechanistic study indicated the alkylation reaction underwent a stepwise transfer hydrogenation, aldol condensation, and hydrogenation reaction pathway.

Original languageEnglish
Pages (from-to)4113-4120
Number of pages8
JournalJournal of Organic Chemistry
Volume82
Issue number8
DOIs
Publication statusPublished - 21 Apr 2017
Externally publishedYes

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Alkylation
Hydrogenation
Alcohols
Ligands
Quinoxalines
Alkylating Agents
Condensation
Atoms
2-picoline
3-hydroxybutanal

Cite this

Feng, Tong Yu ; Li, Hong Xi ; Young, David James ; Lang, Jian Ping. / Ligand-Free RuCl3-Catalyzed Alkylation of Methylazaarenes with Alcohols. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 8. pp. 4113-4120.
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Ligand-Free RuCl3-Catalyzed Alkylation of Methylazaarenes with Alcohols. / Feng, Tong Yu; Li, Hong Xi; Young, David James; Lang, Jian Ping.

In: Journal of Organic Chemistry, Vol. 82, No. 8, 21.04.2017, p. 4113-4120.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Feng, Tong Yu

AU - Li, Hong Xi

AU - Young, David James

AU - Lang, Jian Ping

N1 - Note: The names of compounds 3a,c−f,h−k,m and 4a were corrected on April 5, 2017.

PY - 2017/4/21

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N2 - RuCl3 efficiently catalyzes the alkylation of methylquinolines, methylpyridines, 2-methyl-benzooxazoles, and 2-methyl-quinoxalines with alkyl- or aryl-alcohols as alkylating agents. This synthetically useful and atom economical transformation does not require additional ligands. The mechanistic study indicated the alkylation reaction underwent a stepwise transfer hydrogenation, aldol condensation, and hydrogenation reaction pathway.

AB - RuCl3 efficiently catalyzes the alkylation of methylquinolines, methylpyridines, 2-methyl-benzooxazoles, and 2-methyl-quinoxalines with alkyl- or aryl-alcohols as alkylating agents. This synthetically useful and atom economical transformation does not require additional ligands. The mechanistic study indicated the alkylation reaction underwent a stepwise transfer hydrogenation, aldol condensation, and hydrogenation reaction pathway.

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