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Synthesis of Functionalized 1‐Substituted Alkenylsilanols and Establishment of Conditions for Their Palladium‐Catalyzed Cross‐Coupling Reactions To Afford 1‐Substituted Styrene Derivatives
Author(s) -
Ghosh Sunil K.,
Singh Rekha,
Singh Gobind C.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400339
Subject(s) - chemistry , silanes , palladium , aryl , catalysis , styrene , reactivity (psychology) , tetrabutylammonium fluoride , coupling reaction , copper , organic chemistry , chloride , fluoride , polymer chemistry , combinatorial chemistry , inorganic chemistry , silane , alkyl , copolymer , medicine , polymer , alternative medicine , pathology
An efficient method for the quantitative conversion of 1‐substituted alkenyl(phenyl)silanes into the corresponding alkenylsilanols has been developed and used in their palladium(0)‐catalyzed, tetrabutylammonium fluoride‐promoted cross‐coupling reaction with aryl iodides. Copper( I ) chloride modulated the reactivity of TBAF in such a way that it virtually eliminated the protiodesilylation of alkenylsilanols, thus favoring the formation of ipso ‐coupled products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)