A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

Abstract

A one‐pot transition‐metal‐free synthesis of styrenyl ethers starting from 2‐aryloxy/alkoxy acetophenones is described. The protocol explores the use of tosyl hydrazide and potassium carbonate as a mild base via Bamford‐Stevens reaction to synthesize the styrenyl ethers. The protocol is very simple, practical and uses mild reaction conditions with simple reaction set‐up. This practical protocol proved to be scalable on gram quantity.

Bamford‐Stevens and Shapiro Reactions in Organic Synthesis

“…In 2018, Bhat reported transition metal free synthesis of styrenyl ethers from 2‐aryloxy/alkoxy acetophenones (scheme 6). [20] A range of α‐alkoxy‐, α‐aryloxy ketones 35 were converted to tosylhydrazones, which were then treated with potassium carbonate in 1,4‐dioxane at 110 °C. Authors developed a procedure to perform both steps in one pot and reported moderate to good (65–84%) yields with mostly Z ‐selective products 36 .…”

Formation of a Sterically Crowded 1,6,6αλ4-Triselenapentalene and 4H-Selenopyran-4-selones Fused with Two Bornane Skeletons Through the Reaction of d-Camphor p-Toluenesulfonylhydrazone With a Base and Elemental Selenium

“…In the course of our successive studies on the synthesis of higher-row chalcogenocarbonyl compounds, we have found a convenient synthesis of dialkenyl diselenides C through the reaction of ptoluenesulfonylhydrazones A, derived from ketones possessing an α-methylene group, with a base and elemental selenium. [18][19][20][21][22][23][24] The reaction was assumed to proceed through the in situ generated alkeneselenolate ions B via Bamford-Stevens type reaction of ptoluenesulfonylhydrazones [25][26][27][28][29][30][31][32][33] as shown in Scheme 1, and, therefore, the synthetic application of this sequence to the preparation of various selenium-containing heterocyclic compounds was keenly expected.…”