/ E-Alerts

Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions

Shrikant D. Tambe, Kwan Hong Min, Naeem Iqbal and Eun Jin Cho

Beilstein J. Org. Chem. 2020, 16, 1335–1342. https://doi.org/10.3762/bjoc.16.114

Supporting Information

Supporting Information File 1: Additional experimental details and analytical data.
Format: PDF	Size: 3.4 MB	Download
Supporting Information File 2: Crystal data for 3a.
Format: CIF	Size: 507.3 KB	Download

Cite the Following Article

Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions

Shrikant D. Tambe, Kwan Hong Min, Naeem Iqbal and Eun Jin Cho

Beilstein J. Org. Chem. 2020, 16, 1335–1342. https://doi.org/10.3762/bjoc.16.114

How to Cite

Tambe, S. D.; Min, K. H.; Iqbal, N.; Cho, E. J. Beilstein J. Org. Chem. 2020, 16, 1335–1342. doi:10.3762/bjoc.16.114

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

File format:

RIS

BibTeX

Include:

Citation for the article above

Citation and complete reference list for the article above

Download

TY  - JOUR
A1  - Tambe, Shrikant D.
A1  - Min, Kwan Hong
A1  - Iqbal, Naeem
A1  - Cho, Eun Jin
T1  - Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions
JF  - Beilstein Journal of Organic Chemistry
PY  - 2020///
VL  - 16
SP  - 1335
EP  - 1342
SN  - 1860-5397
DO  - 10.3762/bjoc.16.114
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.16.114
KW  - 1,2-diamine
KW  - diversity
KW  - imine
KW  - photocatalysis
KW  - visible light
N2  - A simple photocatalytic method was developed for the synthesis of unsymmetrical 1,2-diamines by the unprecedented reductive coupling of N-benzylidene-[1,1'-biphenyl]-2-amines with an aliphatic amine. The presence of a phenyl substituent in the aniline moiety of the substrate was critical for the reactivity. The reaction proceeded via radical–radical cross-coupling of α-amino radicals generated by proton-coupled single-electron transfer in the presence of an Ir photocatalyst. On the other hand, symmetrical 1,2-diamines were selectively produced from the same starting materials by the judicious choice of the reaction conditions, showcasing the distinct reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines. The developed method can be employed for the synthesis of various bulky vicinal diamines, which are potential ligands in stereoselective synthesis.
ER  -

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG	Size: 147.2 KB	Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

Murray, P. R. D.; Cox, J. H.; Chiappini, N. D.; Roos, C. B.; McLoughlin, E. A.; Hejna, B. G.; Nguyen, S. T.; Ripberger, H. H.; Ganley, J. M.; Tsui, E.; Shin, N. Y.; Koronkiewicz, B.; Qiu, G.; Knowles, R. R. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis. Chemical reviews 2021, 122, 2017–2291. doi:10.1021/acs.chemrev.1c00374

Explore citations to this article at

Back To Article

Other Beilstein-Institut Open Science Activities

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)