Potassium alkenylaryltrifluoroborates from haloaryltrifluoroborates via Mizoroki-Heck reaction

Title
Potassium alkenylaryltrifluoroborates from haloaryltrifluoroborates via Mizoroki-Heck reaction
Authors
김태정정규혁송중호함정엽
Keywords
Potassium trifluoroborate; alkene; Suzuki-Miyaura; Mizoroki-Heck; palladium; cross-coupling; stilbene
Issue Date
2013-10
Publisher
2013 추계 대한화학회
Abstract
Organotrifluoroborate salts have been used as important coupling partners in the Suzuki-Miyaura cross-coupling reaction due to their inherent stability to both air and moisture as well as their easy handling. Moreover, their remarkable tolerance to harsh conditions in a number of reactions has allowed the preparation of functionalized trifluoroborates that may not be synthesized from the corresponding boronic acids or boronate esters. For example, functionalizations of organotrifluoroborates such as epoxidation, dihydroxylation, oxidation, metalation, [3+2] cyclization, and nucleophilic substitution were successfully performed without loss of the BF3K group. In particular, Molander and co-workers demonstrated the synthesis of alkenylaryltrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination of the corresponding organotrifluoroborates. Although a number of di- or trisubstituted olefins was successfully prepared in moderate to excellent yields via direct olefination of organotrifluoroborates, these previous methods have limitations, resulting from the inseparable mixture of E/Z isomers and stoichiometric amounts of the phosphate [(EtO2)P=O(OLi)] by-products. Adv. Synth. Catal. 2013, 355, 2459-2465. we report herein the preparation of potassium alkenylaryltrifluoroborates using arylolefins or activated olefins as electrophiles via a Pd-catalyzed Mizoroki-Heck reaction.
URI
http://pubs.kist.re.kr/handle/201004/46076
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KIST Publication > Conference Paper
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