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Manganese(III)‐Catalyzed Oxidative Cyclization of Aryl 1‐Cyanoalk‐5‐ynyl Ketone Systems: A Convenient and General Approach to Cyclopenta[ b ]naphthalene Derivatives
Author(s) -
Wong YingChieh,
Kao TzuTing,
Huang JingKai,
Jhang YiWun,
Chou MingChen,
Shia KakShan
Publication year - 2014
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.201400257
Subject(s) - chemistry , ketone , silylation , aryl , phosphonate , catalysis , naphthalene , combinatorial chemistry , amide , manganese , halogen , functional group , medicinal chemistry , organic chemistry , alkyl , polymer
A convenient and general approach for cyclopenta[ b ]naphthalene derivatives containing a structurally diverse functionality at C‐4 position has been successfully developed, whereby manganese(III) acetate plays a key role to facilitate the tandem 5‐ exo ‐ dig and 6‐ exo / endo cyclization in an efficient manner. Various functional groups, including trimethyl silyl, aryl, ester, ketone, secondary/tertiary amide, phosphonate and halogen, capped on the terminal acetylenic unit are well tolerated under optimal reaction conditions. It is highly conceivable that this novel [6.6.5] framework formation procedure may have broad synthetic utility in light of its operational simplicity and high yields.