BROWSE

Related Scientist

CCHF's photo.

CCHF
분자활성 촉매반응 연구단
more info

ITEM VIEW & DOWNLOAD

Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transferHighly Cited Paper

Cited 0 time in webofscience Cited 0 time in scopus
137 Viewed 0 Downloaded
Title
Intermolecular [2π+2σ]-photocycloaddition enabled by triplet energy transfer
Author(s)
Kleinmans, Roman; Pinkert, Tobias; Dutta, Subhabrata; Paulisch, Tiffany O.; Hyeyun Keum; Daniliuc, Constantin G.; Glorius, Frank
Publication Date
2022-05
Journal
Nature, v.605, no.7910, pp.477 - 482
Publisher
Nature Research
Abstract
© 2022, The Author(s), under exclusive licence to Springer Nature Limited.For more than one century, photochemical [2+2]-cycloadditions have been used by synthetic chemists to make cyclobutanes, four-membered carbon-based rings. In this reaction, typically two olefin subunits (two π-electrons per olefin) cyclize to form two new C–C σ-bonds. Although the development of photochemical [2+2]-cycloadditions has made enormous progress within the last century, research has been focused on such [2π+2π]-systems, in which two π-bonds are converted into two new σ-bonds1,2. Here we report an intermolecular [2+2]-photocycloaddition that uses bicyclo[1.1.0]butanes as 2σ-electron reactants3–7. This strain-release-driven [2π+2σ]-photocycloaddition reaction was realized by visible-light-mediated triplet energy transfer catalysis8,9. A simple, modular and diastereoselective synthesis of bicyclo[2.1.1]hexanes from heterocyclic olefin coupling partners, namely coumarins, flavones and indoles, is disclosed. Given the increasing importance of bicyclo[2.1.1]hexanes as bioisosteres—groups that convey similar biological properties to those they replace—in pharmaceutical research and considering their limited access10,11, there remains a need for new synthetic methodologies. Applying this strategy enabled us to extend the intermolecular [2+2]-photocycloadditions to σ-bonds and provides previously inaccessible structural motifs.
URI
https://pr.ibs.re.kr/handle/8788114/11705
DOI
10.1038/s41586-022-04636-x
ISSN
0028-0836
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
Files in This Item:
There are no files associated with this item.

qrcode

  • facebook

    twitter

  • Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.
해당 아이템을 이메일로 공유하기 원하시면 인증을 거치시기 바랍니다.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse