Enzymatic halogenation of the phenolic monoterpenes thymol and carvacrol with chloroperoxidase
The conversion of the phenolic monoterpenes thymol and carvacrol into antimicrobials by (electro)-chemoenzymatic halogenation was investigated using a chloroperoxidase (CPO) catalyzed process. The CPO catalysed process enables for the first time the biotechnological production of chlorothymol, chlorocarvacrol and bromothymol as well as a dichlorothymol with high conversion rates, total turnover numbers and space time yields of up to 90%, 164000 and 4.6 mM h -1, respectively.
Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst
We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.
Dinh, Andrew N.,Maddox, Sean M.,Vaidya, Sagar D.,Saputra, Mirza A.,Nalbandian, Christopher J.,Gustafson, Jeffrey L.
p. 13895 - 13905
(2020/11/03)
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