Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes

Cooperative Iodide Pd(0)‐Catalysed Coupling of Alkoxyallenes and N‐Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

“…[18] Nevertheless, great attention is still paid to their preparation. In our laboratory we have been studying 1,2-alkoxydiene reactivity in Heck reactions and a-ary-lated-a,b-enals (Scheme 1), [22] and dihydrobenzofurans and indolidines [23] have been prepared in ac ascaded omino process. In our laboratory we have been studying 1,2-alkoxydiene reactivity in Heck reactions and a-ary-lated-a,b-enals (Scheme 1), [22] and dihydrobenzofurans and indolidines [23] have been prepared in ac ascaded omino process.…”

“…lated-a,b-enals (Scheme 1), [22] and dihydrobenzofurans and indolidines [23] have been prepared in ac ascaded omino process. Alkoxyallenes ease of synthesisa nd exceptional reactivity make them unusual and versatile buildingb locks.…”

The Heck Reaction Applied to 1,3- and 1,2-Unsaturated Derivatives, a Way towards Molecular Complexity

“…Recently, in our laboratory some attention has been paid to the reactivity of protected 1,2-dien-1-ols in the Heck reaction conditions. A new synthetic method for the preparation of α-arylated α,β-unsaturated aldehydes ( 26 ) has been proposed [ 17 ]. Protected dienols 24 were prepared from the corresponding alkynes 23 by reaction with butyllithium ( Scheme 10 ).…”

Synthesis of Highly Functionalised Dihydrobenzofurans and Indolines by Palladium‐Catalysed Mizoroki–Heck–Heteroannulation Cascade Reactions of Alkoxy‐1,3‐dienes

“…In recent years, this reaction has been exploited as a route to a wide variety of hetero-and carbocycles by using 1,2-, 1,3-and 1,4-dienes, as well as internal alkynes, which were treated with aryl or vinyl halides and triflates. [1][2][3] We have previously described the use of the Heck coupling reaction of 1-alkoxy-functionalised 1,3-dienes in synthesis, [4,5] and more recently we turned our attention to protected 3-alkyl-1,2-dienols as synthetic precursors of α-arylated α,β-unsaturated aldehydes [6] and substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofurans and indolines. [7] The general reactivity of conjugated dienes and the direct formation of their palladium-π-allyl complexes has already been described by Heck.…”