Cyclopropanation of Terminal Alkenes through Sequential Atom‐Transfer Radical Addition/1,3‐Elimination

Tappin, Nicholas D. C.; Michalska, Weronika; Rohrbach, Simon; Renaud, Philippe (2019). Cyclopropanation of Terminal Alkenes through Sequential Atom‐Transfer Radical Addition/1,3‐Elimination. Angewandte Chemie, 131(40), pp. 14378-14382. Wiley 10.1002/ange.201907962

[img] Text
Tappin_et_al-2019-Angewandte_Chemie.pdf - Published Version
Restricted to registered users only
Available under License Publisher holds Copyright.

Download (1MB) | Request a copy
[img]
Preview
Text
accepted article boris.pdf - Accepted Version
Available under License Publisher holds Copyright.

Download (414kB) | Preview

An operationally simple method to affect an atom‐transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one‐pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non‐terminal alkenes and electron‐deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Tappin, Nicholas David Charles and Renaud, Philippe

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0044-8249

Publisher:

Wiley

Language:

English

Submitter:

Franziska Bornhauser-Rufer

Date Deposited:

06 Feb 2020 15:18

Last Modified:

23 Jul 2020 02:30

Publisher DOI:

10.1002/ange.201907962

BORIS DOI:

10.7892/boris.138844

URI:

https://boris.unibe.ch/id/eprint/138844

Actions (login required)

Edit item Edit item
Provide Feedback