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Tunable Dimerization and Trimerization of β‐Alkynyl Ketones via Silver Catalysis for Accessing Spiro and Dispiro Compounds Containing 1 H ‐Isochromene
Author(s) -
Wang Dan,
Liu Shuai,
Lan XinChan,
Paniagua Armando,
Hao WenJuan,
Li Guigen,
Tu ShuJiang,
Jiang Bo
Publication year - 2017
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.201700543
Subject(s) - chemistry , catalysis , moiety , cycloaddition , pyridine , methylene , surface modification , medicinal chemistry , combinatorial chemistry , polymer chemistry , stereochemistry , organic chemistry
New silver‐catalyzed tunable dimerization and trimerization reactions of β‐alkynyl ketones have been established, enabling multiple C−C bond‐forming events to selectively access skeletally diverse spiroisochromenes with generally good yields. The silver‐enabled bicycloaddition of β‐alkynyl ketones with water offered hydroxylated spiroisochromenes. Without water, spiroisochromenes with a methylene moiety were obtained through catalytic 6‐ endo‐dig oxo ‐cyclization/[4+2] cycloaddition cascades by using pyridine as additive whereas employment of 1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate (BiNPO 4 H) as a Brønsted acid catalyst rendered the unprecedented dispiro trimerization products through double C( sp 3 )–H functionalization.