Premium
Gold(I)‐Catalyzed Cyclodehydration Enabled by the Triisopropylsilyl Group: A Synthetically Versatile Methodology
Author(s) -
Usanov Dmitry L.,
Naodovic Marina,
Brasholz Malte,
Yamamoto Hisashi
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200176
Subject(s) - chemistry , fulvenes , scheme (mathematics) , generality , group (periodic table) , catalysis , combinatorial chemistry , table (database) , organic chemistry , database , computer science , mathematics , psychology , mathematical analysis , psychotherapist
of a triisopropylsilyl group into allyl and allenyl carbinols greatly enhances the efficiency of gold(I)‐catalyzed cyclodehydration, which can provide rapid access to a library of various compounds including 1 H ‐indenes ( Table 2 and Scheme 5 ), benzofulvenes ( Table 3 ), indan‐2‐ones ( Scheme 2 ), fulvenes ( Table 4 ), cyclopentadienes ( Table 4 ), 5 H ‐dibenzo[ a , c ][7]annulenes ( Scheme 6 ) and dibenzosuberones ( Scheme 6 ). The developed method enables unprecedented product generality for several classes of cyclodehydration reactions, which is particularly notable for the preparation of 1 H ‐indenes. The first synthesis of non‐benzo‐fused fulvenes via cyclodehydration of allenyl vinyl carbinols could be accomplished. The protocol is remarkable for mild conditions, operational convenience, and easy access to starting materials.