DBPP

CAS 2668-47-5, Cat. No EN300-18538065
Reagent for photoreduction

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2,6-Di-tert-butyl-4-phenylphenol (DBPP) is a sterically hindered phenolic photocatalyst that functions as an exceptionally strong organic photoreductant via its phenolate anion excited state. Upon deprotonation and visible-light irradiation, DBPP generates a highly reducing species (E* ≈ −3.16 V vs SCE), placing it among the most powerful metal-free photoreductants known. DBPP is shown to enable deeply reductive photochemistry that is inaccessible to conventional Ir/Ru photoredox catalysts¹. It efficiently promotes single-electron transfer into inert π-systems, including benzene rings, epoxides, aliphatic esters², and benzylic protecting groups, initiating mesolytic bond cleavage. This photoreductant is the key photocatalyst for visible-light debenzylation of C–N and C–O bonds³. It enables hydrogen-free, transition-metal-free removal of benzyl, Cbz, PMB, BOM, and related protecting groups from amides, amines, ethers, esters, carbamates, carbohydrates, peptides, pharmaceuticals, and natural products. The method shows exceptional chemo- and regioselectivity, tolerating alkenes, heterocycles, acids, esters, acetals, and orthogonal protecting groups, and is scalable to multigram (50 mmol) reactions. Taken together, DBPP represents a general-purpose organic “super-reductant” photocatalyst, enabling epoxide activation, ester reduction, cross-coupling initiation, and highly selective photochemical debenzylation under mild conditions.

Synonyms: [1,1'-biphenyl]-4-ol, 3,5-bis(1,1-dimethylethyl)-; 2,6-ditert-butyl-4-phenylphenol; 3,5-di-tert-butylbiphenyl-4-ol; 2,6-ditert-butyl-4-phenyl-phenol; 3,5-di-tert-butyl-[1,1'-biphenyl]-4-ol