Photocascade chemoselective controlling of ambident thio(seleno)cyanates with alkenes via catalyst modulation

Injamam Ul Hoque, Apurba Samanta, Shyamal Pramanik, Soumyadeep Roy Chowdhury, Rabindranath Lo and Soumitra Maity ()
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Injamam Ul Hoque: Indian Institute of Technology (Indian School of Mines)
Apurba Samanta: Indian Institute of Technology (Indian School of Mines)
Shyamal Pramanik: Indian Institute of Technology (Indian School of Mines)
Soumyadeep Roy Chowdhury: Indian Institute of Technology (Indian School of Mines)
Rabindranath Lo: Czech Academy of Sciences
Soumitra Maity: Indian Institute of Technology (Indian School of Mines)

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Controlling the ambident reactivity of thiocyanates in reaction manifolds has been a long-standing and formidable challenge. We report herein a photoredox strategy for installing thiocyanates and isothiocyanates in a controlled chemoselective fashion by manipulating the ambident-SCN through catalyst modulation. The methodology allows redox-, and pot-economical ‘on-demand’ direct access to both hydrothiophene and pyrrolidine heterocycles from the same feedstock alkenes and bifunctional thiocyanomalonates in a photocascade sequence. Its excellent chemoselectivity profile was further expanded to access Se- and N-heterocycles by harnessing selenonitriles. Redox capability of the catalysts, which dictates the substrates to participate in a single or cascade catalytic cycle, was proposed as the key to the present chemodivergency of this process. In addition, detailed mechanistic insights are provided by a conjugation of extensive control experiments and dispersion-corrected density functional theory (DFT) calculations.

Date: 2024
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DOI: 10.1038/s41467-024-49279-w

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