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Synlett
DOI: 10.1055/a-2330-0874
letter

Synthesis of Dihydrobenzosiloles and Silacyclopentane via Double Hydroalumination of Terminal Alkynes

Ryusei Osawa
1   Department of Applied Chemistry, Saitama University, Saitama, Japan
,
Kotaro Ogihara
1   Department of Applied Chemistry, Saitama University, Saitama, Japan
,
Fumine Hamasaki
1   Department of Applied Chemistry, Saitama University, Saitama, Japan
,
Hidenori Kinoshita
2   Department of Applied Chemistry, Saitama University, Saitama, Japan
,
Katsukiyo Miura
3   Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama, Japan
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We developed an efficient method for the synthesis of dihydrobenzosiloles in 19% to 90% isolated yields from 1-hydrosilyl-2-ethynylbenzenes using two equivalents of diisobutylaluminum hydride. The reaction mechanism involves regioselective double hydroalumination of the alkyne moiety followed by cyclization to 2-alanyldihydrobenzosilole. A silacyclopentane was also synthesized in 97% isolated yield from the corresponding 4-silylbut-1-yne under the same reaction conditions. Although the substrate scope was conducted on a 0.5 mmol scale, a gram-scale reaction of 1-diphenylsilyl-2-ethynylbenzene under the optimized reaction conditions successfully afforded the desired product in 94% isolated yield without loss of reactivity.



Publication History

Received: 30 April 2024

Accepted after revision: 18 May 2024

Accepted Manuscript online:
18 May 2024

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