Brønsted acid catalysis of photosensitized cycloadditions. Issue 3 (9th December 2019)
- Record Type:
- Journal Article
- Title:
- Brønsted acid catalysis of photosensitized cycloadditions. Issue 3 (9th December 2019)
- Main Title:
- Brønsted acid catalysis of photosensitized cycloadditions
- Authors:
- Sherbrook, Evan M.
Jung, Hoimin
Cho, Dasol
Baik, My-Hyun
Yoon, Tehshik P. - Abstract:
- Abstract : Brønsted acids can catalyze triplet energy transfer reactions, and DFT computations suggest the unexpected importance of reorganization energy for catalysis. Abstract : Catalysis is central to contemporary synthetic chemistry. There has been a recent recognition that the rates of photochemical reactions can be profoundly impacted by the use of Lewis acid catalysts and co-catalysts. Herein, we show that Brønsted acids can also modulate the reactivity of excited-state organic reactions. Brønsted acids dramatically increase the rate of Ru(bpy)3 2+ -sensitized [2 + 2] photocycloadditions between C -cinnamoyl imidazoles and a range of electron-rich alkene reaction partners. A combination of experimental and computational studies supports a mechanism in which the Brønsted acid co-catalyst accelerates triplet energy transfer from the excited-state [Ru*(bpy)3 ] 2+ chromophore to the Brønsted acid activated C -cinnamoyl imidazole. Computational evidence further suggests the importance of driving force as well as geometrical reorganization, in which the protonation of the imidazole decreases the reorganization penalty during the energy transfer event.
- Is Part Of:
- Chemical science. Volume 11:Issue 3(2020)
- Journal:
- Chemical science
- Issue:
- Volume 11:Issue 3(2020)
- Issue Display:
- Volume 11, Issue 3 (2020)
- Year:
- 2020
- Volume:
- 11
- Issue:
- 3
- Issue Sort Value:
- 2020-0011-0003-0000
- Page Start:
- 856
- Page End:
- 861
- Publication Date:
- 2019-12-09
- Subjects:
- Chemistry -- Periodicals
540.5 - Journal URLs:
- http://pubs.rsc.org/en/Journals/JournalIssues/SC ↗
http://www.rsc.org/ ↗ - DOI:
- 10.1039/c9sc04822g ↗
- Languages:
- English
- ISSNs:
- 2041-6520
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 3151.490000
British Library DSC - BLDSS-3PM
British Library STI - ELD Digital store - Ingest File:
- 12697.xml