Ruthenium-Catalyzed Sequential Hydrosilylation/Dehydrogenation and C-H Silylation: Synthesis of Six-Membered Indole Silacycles and Pyrrole Silyl Ether Cycles

Jiefang Li; Shanshan Xu; Jieyu Liang; Juanjuan Zheng; Ping Li; Jun Wang; Bin Li

doi:10.1021/acs.orglett.4c01949

Ruthenium-Catalyzed Sequential Hydrosilylation/Dehydrogenation and C-H Silylation: Synthesis of Six-Membered Indole Silacycles and Pyrrole Silyl Ether Cycles

Jiefang Li
, Shanshan Xu
, Jieyu Liang
, Juanjuan Zheng
, Ping Li
, Jun Wang
, Bin Li^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

11 Citations (Scopus)

Abstract

Selective dehydrogenative C-H silylation is one of the most powerful tools to synthesize silacycles. Herein, we developed Ru-catalyzed sequential hydrosilylation/C-H silylation of allyl-indoles and dehydrogenative O-H/C-H silylation of pyrrole phenols. Both six-membered indole silacycles and pyrrole silyl ether cycles were successfully synthesized with good functional group tolerance. Furthermore, the RuHCl(CO)(PPh₃)₃ catalyst exhibited high reaction compatibility in hydrosilylation of alkene, dehydrogenative O-H silylation, and C-H silylation.

Original language	English
Pages (from-to)	6142-6147
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	29
Early online date	12 Jul 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c01949
Publication status	Published - 26 Jul 2024

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10.1021/acs.orglett.4c01949

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@article{2b8c23dd9e33478699f3ac0f8f7a7960,

title = "Ruthenium-Catalyzed Sequential Hydrosilylation/Dehydrogenation and C-H Silylation: Synthesis of Six-Membered Indole Silacycles and Pyrrole Silyl Ether Cycles",

abstract = "Selective dehydrogenative C-H silylation is one of the most powerful tools to synthesize silacycles. Herein, we developed Ru-catalyzed sequential hydrosilylation/C-H silylation of allyl-indoles and dehydrogenative O-H/C-H silylation of pyrrole phenols. Both six-membered indole silacycles and pyrrole silyl ether cycles were successfully synthesized with good functional group tolerance. Furthermore, the RuHCl(CO)(PPh3)3 catalyst exhibited high reaction compatibility in hydrosilylation of alkene, dehydrogenative O-H silylation, and C-H silylation.",

author = "Jiefang Li and Shanshan Xu and Jieyu Liang and Juanjuan Zheng and Ping Li and Jun Wang and Bin Li",

note = "The authors thank the Support of the Foundation of Department of Education of Guangdong Province (2021ZDZX2045) and the Foundation of Wuyi University (2021WGALH06). Publisher Copyright: {\textcopyright} 2024 American Chemical Society",

year = "2024",

month = jul,

day = "26",

doi = "10.1021/acs.orglett.4c01949",

language = "English",

volume = "26",

pages = "6142--6147",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "29",

}

TY - JOUR

T1 - Ruthenium-Catalyzed Sequential Hydrosilylation/Dehydrogenation and C-H Silylation

T2 - Synthesis of Six-Membered Indole Silacycles and Pyrrole Silyl Ether Cycles

AU - Li, Jiefang

AU - Xu, Shanshan

AU - Liang, Jieyu

AU - Zheng, Juanjuan

AU - Li, Ping

AU - Wang, Jun

AU - Li, Bin

N1 - The authors thank the Support of the Foundation of Department of Education of Guangdong Province (2021ZDZX2045) and the Foundation of Wuyi University (2021WGALH06). Publisher Copyright: © 2024 American Chemical Society

PY - 2024/7/26

Y1 - 2024/7/26

N2 - Selective dehydrogenative C-H silylation is one of the most powerful tools to synthesize silacycles. Herein, we developed Ru-catalyzed sequential hydrosilylation/C-H silylation of allyl-indoles and dehydrogenative O-H/C-H silylation of pyrrole phenols. Both six-membered indole silacycles and pyrrole silyl ether cycles were successfully synthesized with good functional group tolerance. Furthermore, the RuHCl(CO)(PPh3)3 catalyst exhibited high reaction compatibility in hydrosilylation of alkene, dehydrogenative O-H silylation, and C-H silylation.

AB - Selective dehydrogenative C-H silylation is one of the most powerful tools to synthesize silacycles. Herein, we developed Ru-catalyzed sequential hydrosilylation/C-H silylation of allyl-indoles and dehydrogenative O-H/C-H silylation of pyrrole phenols. Both six-membered indole silacycles and pyrrole silyl ether cycles were successfully synthesized with good functional group tolerance. Furthermore, the RuHCl(CO)(PPh3)3 catalyst exhibited high reaction compatibility in hydrosilylation of alkene, dehydrogenative O-H silylation, and C-H silylation.

UR - https://www.scopus.com/pages/publications/85198566300

U2 - 10.1021/acs.orglett.4c01949

DO - 10.1021/acs.orglett.4c01949

M3 - Journal article

C2 - 38995672

AN - SCOPUS:85198566300

SN - 1523-7060

VL - 26

SP - 6142

EP - 6147

JO - Organic Letters

JF - Organic Letters

IS - 29

ER -

Ruthenium-Catalyzed Sequential Hydrosilylation/Dehydrogenation and C-H Silylation: Synthesis of Six-Membered Indole Silacycles and Pyrrole Silyl Ether Cycles

Abstract

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