Access to 2,2-Halofluorobicyclo[1.1.1] Pentanes via Non Ozone-Depleting Ethyl Dihalofluoroacetate

Ziyue Zhu; Jiaqi Tang; Matthew Coe; Alexander Knieb; Yijie Xu; Daniel Lin; Chao Zhang; G. K. Surya Prakash

doi:10.1002/adsc.202401475

Access to 2,2-Halofluorobicyclo[1.1.1] Pentanes via Non Ozone-Depleting Ethyl Dihalofluoroacetate

Ziyue Zhu
, Jiaqi Tang
, Matthew Coe
, Alexander Knieb
, Yijie Xu
, Daniel Lin
, Chao Zhang
, G. K. Surya Prakash

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

11 Scopus citations

Abstract

An operationally simple protocol to access 2,2-chlorofluoro-, and 2,2-bromofluorobicyclopentanes (BCPs) via commercially available, inexpensive, non-ozone depleting, and bench stable reagents is reported. The resulting BCP products are tolerated in diverse, synthetically relevant post-functionalization reactions. Gram-scale reactions to prepare the BCPs are also included.

Original language	English (US)
Article number	e202401475
Journal	Advanced Synthesis and Catalysis
Volume	367
Issue number	6
DOIs	https://doi.org/10.1002/adsc.202401475
State	Published - Mar 18 2025
Externally published	Yes

Keywords

2-halofluorobicyclopentanes
Bromofluorocarbene
Chlorofluorocarbene
Ethyl dibromofluoroacetate
Ethyl dichlorofluoroacetate

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.202401475

Cite this

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title = "Access to 2,2-Halofluorobicyclo[1.1.1] Pentanes via Non Ozone-Depleting Ethyl Dihalofluoroacetate",

abstract = "An operationally simple protocol to access 2,2-chlorofluoro-, and 2,2-bromofluorobicyclopentanes (BCPs) via commercially available, inexpensive, non-ozone depleting, and bench stable reagents is reported. The resulting BCP products are tolerated in diverse, synthetically relevant post-functionalization reactions. Gram-scale reactions to prepare the BCPs are also included.",

keywords = "2-halofluorobicyclopentanes, Bromofluorocarbene, Chlorofluorocarbene, Ethyl dibromofluoroacetate, Ethyl dichlorofluoroacetate",

author = "Ziyue Zhu and Jiaqi Tang and Matthew Coe and Alexander Knieb and Yijie Xu and Daniel Lin and Chao Zhang and \{Surya Prakash\}, \{G. K.\}",

note = "Publisher Copyright: 2025 The Author(s). Advanced Synthesis \& Catalysis published by Wiley-VCH GmbH.",

year = "2025",

month = mar,

day = "18",

doi = "10.1002/adsc.202401475",

language = "English (US)",

volume = "367",

journal = "Advanced Synthesis and Catalysis",

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publisher = "Wiley-VCH Verlag",

number = "6",

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TY - JOUR

T1 - Access to 2,2-Halofluorobicyclo[1.1.1] Pentanes via Non Ozone-Depleting Ethyl Dihalofluoroacetate

AU - Zhu, Ziyue

AU - Tang, Jiaqi

AU - Coe, Matthew

AU - Knieb, Alexander

AU - Xu, Yijie

AU - Lin, Daniel

AU - Zhang, Chao

AU - Surya Prakash, G. K.

N1 - Publisher Copyright: 2025 The Author(s). Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

PY - 2025/3/18

Y1 - 2025/3/18

N2 - An operationally simple protocol to access 2,2-chlorofluoro-, and 2,2-bromofluorobicyclopentanes (BCPs) via commercially available, inexpensive, non-ozone depleting, and bench stable reagents is reported. The resulting BCP products are tolerated in diverse, synthetically relevant post-functionalization reactions. Gram-scale reactions to prepare the BCPs are also included.

AB - An operationally simple protocol to access 2,2-chlorofluoro-, and 2,2-bromofluorobicyclopentanes (BCPs) via commercially available, inexpensive, non-ozone depleting, and bench stable reagents is reported. The resulting BCP products are tolerated in diverse, synthetically relevant post-functionalization reactions. Gram-scale reactions to prepare the BCPs are also included.

KW - 2-halofluorobicyclopentanes

KW - Bromofluorocarbene

KW - Chlorofluorocarbene

KW - Ethyl dibromofluoroacetate

KW - Ethyl dichlorofluoroacetate

UR - https://www.scopus.com/pages/publications/105001065886

UR - https://www.scopus.com/pages/publications/105001065886#tab=citedBy

U2 - 10.1002/adsc.202401475

DO - 10.1002/adsc.202401475

M3 - Article

AN - SCOPUS:105001065886

SN - 1615-4150

VL - 367

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 6

M1 - e202401475

ER -

Access to 2,2-Halofluorobicyclo[1.1.1] Pentanes via Non Ozone-Depleting Ethyl Dihalofluoroacetate

Abstract

Keywords

ASJC Scopus subject areas

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