Divergent Synthesis of Silacycles by Ligand-Controlled Rhodium-Catalyzed Annulation of (2-Hydrosilylaryl)acetylenes

被引:0
|
作者
Fuji, Kazuto [2 ]
Kawashima, Kyohei [1 ]
Mori, Toshifumi [1 ,2 ]
Sekine, Kohei [1 ,2 ]
Kuninobu, Yoichiro [1 ,2 ]
机构
[1] Kyushu Univ, Inst Mat Chem & Engn, 6-1 Kasugakoen, Kasuga Shi, Fukuoka 8168580, Japan
[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Dept Interdisciplinary Engn Sci, Kasuga Shi, Fukuoka 8168580, Japan
关键词
HYDRIDE-PROMOTED CYCLIZATION; TRANS-HYDROSILYLATION; ALKYNES; BENZOSILOLES; HETEROCYCLES; DERIVATIVES; SITE;
D O I
10.1021/acs.orglett.4c04694
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This study demonstrates the rhodium-catalyzed divergent synthesis of 5-, 5,6-, and 8-membered silacyclic compounds, such as benzosilole, silolosiline, and disilocine, from (2-hydrosilylaryl)acetylenes. To achieve high product selectivity, intra- and intermolecular reactions are controlled by tuning the mono- and bidentate phosphine ligands on the rhodium catalyst precursor. Deuterium labeling experiments and computational studies reveal that the annulation reaction proceeds via hydride transfer to the alkyne moiety.
引用
收藏
页码:1614 / 1619
页数:6
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