Boron Trifluoride-Mediated Domino Dehydration/Electrophilic Cyclization of Silylalkynols Leading to 2,3-Fused Tricyclic Benzofulvenes

Takashi Okitsu; Takeshi Yoshikawa; Mai Morohashi; Kokoro Aoki; Takayuki Yakura; Ken Sakata; Manabu Hatano

doi:10.1021/acs.orglett.4c00123

Boron Trifluoride-Mediated Domino Dehydration/Electrophilic Cyclization of Silylalkynols Leading to 2,3-Fused Tricyclic Benzofulvenes

Takashi Okitsu^*, Takeshi Yoshikawa^*, Mai Morohashi, Kokoro Aoki, Takayuki Yakura, Ken Sakata, Manabu Hatano

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

Abstract

A BF₃-mediated domino dehydration/electrophilic cyclization of silylalkynols to form 2,3-fused tricyclic benzofulvenes was achieved. In the latter step, in situ generated BF₃·OH₂ enables the electrophilic activation of alkynes. The predominant Z-selectivity of the reaction is also discussed.

Original language	English
Pages (from-to)	1652-1656
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.4c00123
State	Published - 2024/03/01

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c00123

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title = "Boron Trifluoride-Mediated Domino Dehydration/Electrophilic Cyclization of Silylalkynols Leading to 2,3-Fused Tricyclic Benzofulvenes",

abstract = "A BF3-mediated domino dehydration/electrophilic cyclization of silylalkynols to form 2,3-fused tricyclic benzofulvenes was achieved. In the latter step, in situ generated BF3·OH2 enables the electrophilic activation of alkynes. The predominant Z-selectivity of the reaction is also discussed.",

author = "Takashi Okitsu and Takeshi Yoshikawa and Mai Morohashi and Kokoro Aoki and Takayuki Yakura and Ken Sakata and Manabu Hatano",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society",

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doi = "10.1021/acs.orglett.4c00123",

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T1 - Boron Trifluoride-Mediated Domino Dehydration/Electrophilic Cyclization of Silylalkynols Leading to 2,3-Fused Tricyclic Benzofulvenes

AU - Okitsu, Takashi

AU - Yoshikawa, Takeshi

AU - Morohashi, Mai

AU - Aoki, Kokoro

AU - Yakura, Takayuki

AU - Sakata, Ken

AU - Hatano, Manabu

PY - 2024/3/1

Y1 - 2024/3/1

N2 - A BF3-mediated domino dehydration/electrophilic cyclization of silylalkynols to form 2,3-fused tricyclic benzofulvenes was achieved. In the latter step, in situ generated BF3·OH2 enables the electrophilic activation of alkynes. The predominant Z-selectivity of the reaction is also discussed.

AB - A BF3-mediated domino dehydration/electrophilic cyclization of silylalkynols to form 2,3-fused tricyclic benzofulvenes was achieved. In the latter step, in situ generated BF3·OH2 enables the electrophilic activation of alkynes. The predominant Z-selectivity of the reaction is also discussed.

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U2 - 10.1021/acs.orglett.4c00123

DO - 10.1021/acs.orglett.4c00123

M3 - 学術論文

C2 - 38385717

AN - SCOPUS:85186181056

SN - 1523-7060

VL - 26

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JO - Organic Letters

JF - Organic Letters

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ER -

Boron Trifluoride-Mediated Domino Dehydration/Electrophilic Cyclization of Silylalkynols Leading to 2,3-Fused Tricyclic Benzofulvenes

Abstract

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