Каталитическое гидросилилирование циклоолефинов в присутствии комплексов переходных металлов (обзор)

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Abstract

В обзоре рассмотрены известные на данный момент в литературе реакции каталитического гидросилилирования циклоолефинов в присутствии катализаторов на основе комплексов переходных металлов, таких как платина, родий, кобальт, палладий, никель и др., а также особенности этих реакций: влияние природы циклоолефина и катализатора на реакционную способность, селективность образования различных продуктов и выход реакции. Обсуждается возможность стерео- и энантиоселективного синтеза кремнийуглеводородов с применением этих реакций, а также другие способы проведения гидросилилирования циклоолефинов (под действием кислот Льюиса, термическое и фотокаталитическое гидросилилирование). Показано, что наилучшая стерео- и энантиоселективность гидросилилирования циклоолефинов достигается в присутствии катализаторов на основе Pd с хиральными лигандами (P,N-лиганды на основе ферроцена, бинафтильные лиганды). Тем не менее гидросилилирование под действием комплексов переходных металлов по-прежнему остается недостаточно универсальным способом синтеза силанов с циклическими заместителями из неактивированных (не содержащих хлор) силанов, в отличие от радикального гидросилилирования.

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Дмитрий Александрович Алентьев

Институт нефтехимического синтеза им. А. В. Топчиева РАН

Author for correspondence.
Email: d.alentiev@ips.ac.ru
ORCID iD: 0000-0002-5010-6044

к.х.н.

Russian Federation, Москва

Марина Алексеевна Козлова

Институт нефтехимического синтеза им. А. В. Топчиева РАН

Email: d.alentiev@ips.ac.ru
ORCID iD: 0000-0002-3943-0177

к.х.н.

Russian Federation, Москва

Кирилл Владимирович Зайцев

Институт нефтехимического синтеза им. А. В. Топчиева РАН

Email: d.alentiev@ips.ac.ru
ORCID iD: 0000-0003-3106-8692

д.х.н.

Russian Federation, Москва

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Supplementary files

Supplementary Files
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1. JATS XML
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2. Table 2. Hydrosilylation of substituted bicyclo[2.2.1.1]hept-5-enes under the action of silanes

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3. Table 3. Conditions, yields and configurations of asymmetric carbon atoms of the main products of hydrosilylation reactions of cycloolefins with trichlorosilane

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4. Table 4. Hydrosilylation reactions of cycloolefins with halogen-containing hydrosilanes (0°C, 40 h) [38]

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5. Table 5. Yields and selectivity of hydrosilylation reactions of 1-vinylcycloalkenes with methyldichlorosilane in the presence of PdCl2(PPh3)2 (catalyst K22) at 80°C

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6. Table 6. Reaction conditions for the hydrosilylation of cycloolefins with triethylsilane (XVIII) and reaction product yields

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7. Fig. 1

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8. Fig. 2

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9. Fig. 3

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