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Palladium‐Catalyzed Triple Cyclization of 2,7‐Alkadiynylic Carbonates with 2‐Butyne‐1,4‐diol or 2‐Butyne‐1,4‐disulfonamides
Author(s) -
Song Yulong,
Wu Wangteng,
Fu Chunling,
Huang Xin,
Ma Shengming
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900162
Subject(s) - chemistry , palladium , alkene , catalysis , nucleophile , diol , medicinal chemistry , intermolecular force , triple bond , organic chemistry , double bond , molecule
A palladium‐catalyzed highly E ‐selective triple cyclization of 2,7‐alkadiynylic carbonates with 2‐butyne‐1,4‐diol or 2‐butyne‐1,4‐disulfonamides to construct different tricycles such as 6,8‐dihydrobenzo[1,2‐c:3,4‐c′]difuran‐1(3 H )‐one and 1,3,6,7‐tetrahydro‐8 H ‐furo[3,4‐e]isoindol‐8‐one derivatives has been reported. The alkene group produced and the nucleophilic unit kept in the product provide further opportunity to construct more complicated polycycles. The control experiments showed that the reaction mainly go through an intermolecular insertion of the alkynes before the lactonization or lactamization.