B(C6F5)3-catalyzed synthesis of benzofused-siloles

Liam D. Curless; Michael J. Ingleson

doi:10.1021/om501033p

B(C₆F₅)₃-catalyzed synthesis of benzofused-siloles

Liam D. Curless, Michael J. Ingleson^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The dehydrosilylation of 2-(SiR₂H)-biphenyls catalyzed by B(C₆F₅)₃ and a weak base forms silafluorenes with H₂ as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C₆F₅)₃ also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel-Crafts reaction facilitated by a weak base.

Original language	English
Pages (from-to)	7241-7246
Number of pages	6
Journal	Organometallics
Volume	33
Issue number	24
DOIs	https://doi.org/10.1021/om501033p
Publication status	Published - 22 Dec 2014

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title = "B(C6F5)3-catalyzed synthesis of benzofused-siloles",

abstract = "The dehydrosilylation of 2-(SiR2H)-biphenyls catalyzed by B(C6F5)3 and a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel-Crafts reaction facilitated by a weak base.",

author = "Curless, {Liam D.} and Ingleson, {Michael J.}",

year = "2014",

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doi = "10.1021/om501033p",

language = "English",

volume = "33",

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journal = "Organometallics",

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AU - Curless, Liam D.

AU - Ingleson, Michael J.

PY - 2014/12/22

Y1 - 2014/12/22

N2 - The dehydrosilylation of 2-(SiR2H)-biphenyls catalyzed by B(C6F5)3 and a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel-Crafts reaction facilitated by a weak base.

AB - The dehydrosilylation of 2-(SiR2H)-biphenyls catalyzed by B(C6F5)3 and a weak base forms silafluorenes with H2 as the only byproduct. Attempts to extend this approach to synthesize siloles derived from 2,2′-bithiophenes and N-Me-2-Ph-indole resulted in competing reactivity, including protodesilylation. B(C6F5)3 also catalyzed the one-pot, two-step formation of silaindenes from aryl-alkynes by alkyne trans-hydrosilylation, followed by an intramolecular Sila-Friedel-Crafts reaction facilitated by a weak base.

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U2 - 10.1021/om501033p

DO - 10.1021/om501033p

M3 - Article

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SP - 7241

EP - 7246

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 24

ER -

B(C₆F₅)₃-catalyzed synthesis of benzofused-siloles

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