AI Article Synopsis
- A new method for oxidative coupling of 1,3-enynamides using DMSO as an oxidant has been created.
- This method allows for the efficient alkylation of carbon and various unmodified heteroatom nucleophiles like alcohols, thiols, and hydrazides at the γ-position with high selectivity.
- Kinetic studies indicate that the mechanism varies based on the nucleophile, involving either a concerted S2'' process or a carbocationic mechanism, with remote site-selectivity linked to a positive charge at the terminal carbocationic center.
Article Abstract
Oxidative coupling of 1,3-enynamides using DMSO as a terminal oxidant has been developed. Carbon as well as unmodified heteroatom nucleophiles, including aliphatic alcohols, thiols, and hydrazides, could be efficiently alkylated at the γ-position in a highly regioselective fashion. The kinetic analysis suggested a nucleophile-dependent mechanism ranging from a concerted S2'' to a carbocationic mechanism. Thus, the remote site-selectivity was ascribed to the partial positive charge developing at the terminal carbocationic center.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6849631 | PMC |
| http://dx.doi.org/10.1039/c9sc03663f | DOI Listing |
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