F- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF3-Substituted Indenes

Hai Jun Tang; Yu Feng Zhang; Yi Wen Jiang; Chao Feng

doi:10.1021/acs.orglett.8b02128

F^- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF₃-Substituted Indenes

Hai Jun Tang, Yu Feng Zhang, Yi Wen Jiang, Chao Feng

School of Chemistry and Moleculai Engineering

Nanjing Tech University

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

32 Scopus citations

Abstract

An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.

Original language	English
Pages (from-to)	5190-5193
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.8b02128
State	Published - 7 Sep 2018

Access to Document

10.1021/acs.orglett.8b02128

Cite this

@article{06016ea99dcd42f1ada8a520c0db3cd9,

title = "F- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF3-Substituted Indenes",

abstract = "An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.",

author = "Tang, {Hai Jun} and Zhang, {Yu Feng} and Jiang, {Yi Wen} and Chao Feng",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = sep,

day = "7",

doi = "10.1021/acs.orglett.8b02128",

language = "英语",

volume = "20",

pages = "5190--5193",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - F- Nucleophilic-Addition-Induced [3 + 2] Annulation

T2 - Direct Access to CF3-Substituted Indenes

AU - Tang, Hai Jun

AU - Zhang, Yu Feng

AU - Jiang, Yi Wen

AU - Feng, Chao

PY - 2018/9/7

Y1 - 2018/9/7

N2 - An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.

AB - An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.

UR - http://www.scopus.com/inward/record.url?scp=85052902807&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02128

DO - 10.1021/acs.orglett.8b02128

M3 - 文章

C2 - 30125123

AN - SCOPUS:85052902807

SN - 1523-7060

VL - 20

SP - 5190

EP - 5193

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

F^- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF₃-Substituted Indenes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this