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Synthesis 2023; 55(10): 1577-1585
DOI: 10.1055/a-1992-6926
paper

Synthesis of 2,3-Dihydrosiloles via Palladium-Catalyzed Heck-type Arylation of Silacyclopentenes with Aryl Iodides

Wei-Sheng Huang  ‡
a   College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Fang-Ying Ling‡
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Xiao-Jun Fang
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Yu-Ming Cui
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Fei Ye
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Zheng Xu
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Jian Cao
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
,
Hua Yang 
a   College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China
,
Li-Wen Xu∗
a   College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China
b   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China
› InstitutsangabenThis work was financially supported by grants from the National Natural­ Science Foundation of China (22072035 and 21901056) and the Zhejiang Provincial Natural Science Foundation of China (LY20B030006, LY21B030007, LR22B020002 and LY22B020006).
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Abstract

The transition-metal-catalyzed synthesis of chiral silacycles is a challenging processes in organosilicon chemistry. Herein, we report a facile and regioselective synthesis of a novel class of 2,3-dihydrosilole derivatives with good yields via the palladium-catalyzed Heck-type reaction of silacyclopentenes (SCPs) with aryl iodides. Preliminary investigations on the enantioselective version of this palladium-catalyzed Heck-type process reveal that the presence of N-Boc-l-proline allows the diastereo- and enantioselective formation of chiral 2,3-dihydrosilole derivatives bearing both carbon and silicon-stereogenic centers.

Key words

silacycles - palladium catalysis - Heck arylation - silicon-stereogenic - organosilicon

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1992-6926.
  • Supporting Information


Publikationsverlauf

Eingereicht: 04. November 2022

Angenommen nach Revision: 05. Dezember 2022

Accepted Manuscript online:
05. Dezember 2022

Artikel online veröffentlicht:
10. Januar 2023

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