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Synthesis 2022; 54(10): 2373-2390
DOI: 10.1055/a-1731-3852
DOI: 10.1055/a-1731-3852
feature
A Mild Heteroatom (O-, N-, and S-) Methylation Protocol Using Trimethyl Phosphate (TMP)–Ca(OH)2Combination
Financial support from the Youth Innovation Promotion Association of the Chinese Academy of Sciences (2021251) is acknowledged.
Abstract
A mild heteroatom methylation protocol using trimethyl phosphate (TMP)–Ca(OH)2 combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.
Key words
trimethyl phosphate - calcium hydroxide - heteroatom methylation - aqueous S-methylation - N-sulfonamide methylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1731-3852.
- Supporting Information
Publication History
Received: 16 December 2021
Accepted after revision: 04 January 2022
Accepted Manuscript online:
04 January 2022
Article published online:
03 March 2022
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For toxicity study of TMP, see:
Ca(OH)2 has occasionally been used as a base in organic synthesis. For examples, see: