Palladium-catalyzed allylic allenylation of homoallyl alcohols with propargylic carbonates

Abstract

A palladium-catalyzed reaction of homoallyl acohols with propargylic carbonates was realized via oxidative addition/decarboxylation/retro-allylation. The reaction proceeds with a wide substrate scope by using readily available starting materials, which provides...

Recent Progress in Application of Propargylic Alcohols in Organic Syntheses

“…In Zhou's work, palladium acetate as the catalyst and P[(3,5-(CF 3 ) 2 C 6 H 3 )] 3 as the phosphorus ligand were selected for allenylation of homoallyl alcohols 161 as allyl reagents with propargylic carbonates 160 derived from propargylic alcohols (Scheme 70). [65] Screening other propargylic derivatives did not effective like propargylic carbonates. The reaction involves the oxidative addition of Pd(II) to the CÀ H bond of propargylic carbonates, followed by the insertion of the OÀ H bond to generate intermediate A.…”

Palladium-catalyzed bicyclization of alkynyl aryl iodide with allenyl malonates

“…In the course of our ongoing research on the palladium-catalyzed cross-coupling reaction, 7 a ,13 we here report a palladium-catalyzed bicyclization of alkynyl aryl iodide with allenyl malonates (Scheme 1c).…”

Electrochemical Radical Retro-Allylation of Homoallylic Alcohols with Sulfonyl Hydrazides

“…Since 2006, the Oshima group has successfully achieved retro-allylation of homoallylic alcohols by rhodium, copper, palladium, and nickel catalysts . Very recently, Zhou and co-workers reported a series of works about palladium-catalyzed retro-allylation of homoallylic alcohols with aryl iodides or propargylic carbonates . Although significant progress has been made in the field of retro-allylation, there are still many shortcomings to be addressed, such as the use of transition-metal catalysts and organic phosphine ligands.…”