Alkynyl Borrowing: Silver-Catalyzed Amination of Secondary Propargylic Alcohols via C(sp³)–C(sp) Bond Cleavage

Abstract

The silver-catalyzed alkynyl borrowing amination of secondary propargyl alcohols via C­(sp3)–C­(sp) bond cleavage has been developed. This new strategy was based on the β-alkynyl elimination of propargyl alcohols and alkynyl as the borrowing subject. This alkynyl borrowing amination featured high atom economy, wide functional group tolerance, and high efficiency.

Recent Progress in Application of Propargylic Alcohols in Organic Syntheses

“…In 2022, Luo′s research group used a silver catalyst for the amination of secondary propargylic alcohols 1 with pmethylbenzenesulfonyl amine (TsNH 2 ) 171 access to propargylic amines 172 (Scheme 75). [69] For this purpose, they utilized only 10 mol% of AgBF 4 as a catalyst for the activation of the C( sp 3 )−C( sp ) bond of propargylic alcohols. Notable advantages of this protocol include broad substrate scope tolerance, using no oxidant or additive, and being highly atom economical due to the release of H 2 O as the only by‐product.…”

Transition metal-catalyzed alkynylation reactions via alkynyl carbon–carbon bond cleavage

“…The transformation, termed as an alkynyl borrowing strategy, is efficient over a wide range of secondary propargylic alcohols (Scheme 33). 53…”