A convenient two-step synthesis of Coenzyme Q1

A convenient method for the preparation of Coenzyme Q1 from cheap and readily available 3,4,5-trimethoxytoluene is developed. Coenzyme Q1 is synthesized in a moderate yield by a two-step procedure involving the key reaction of an allyl bromide with Coenzyme Q0 through a redox chain reaction. The reaction is efficient and can be used for the synthesis of other Coenzyme Q compounds.

A Convenient Two-Step Synthesis of Coenzyme Q1

<p>A convenient method for the preparation of Coenzyme Q₁ from the cheap and readily available 3,4,5-Trimethoxytoluene was developed. CoQ₁was synthesized in moderate yield by a two-step procedure involving the key reaction of allyl bromide with CoQ₀through a redox chain reaction. The reaction is efficient and could be used for the synthesis of other CoQ compounds.</p>

A Convenient Two-Step Synthesis of Coenzyme Q1

<p>A convenient method for the preparation of Coenzyme Q₁ from the cheap and readily available 3,4,5-Trimethoxytoluene was developed. CoQ₁was synthesized in moderate yield by a two-step procedure involving the key reaction of allyl bromide with CoQ₀through a redox chain reaction. The reaction is efficient and could be used for the synthesis of other CoQ compounds.</p>

Deciphering the Redox Chain Mechanism in the Catalytic Alkylation of Quinones

Alkylation of p-quinones with allylic and benzylic esters is achieved by using a strong Lewis acid as the catalyst. This transformation likely follows an unusual redox chain mechanism. In this mechanism, quinone undergoes a sequence of reactions: it is reduced to ­hydroquinone (HQ), functionalized in a Lewis acid-catalyzed Friedel–Crafts alkylation, and then oxidized back to quinone. The last step is concurrent with the first step of a second quinone molecule, which is reduced to new HQ and functionalized, and thus propagates the redox chain reaction. The autoinitiation mechanism of the redox chain is not well understood, but additive HQ or Hantzsch ester can serve as effective initiators. The likelihood of this mechanism was elaborated by ­kinetic studies and various control experiments.1 Introduction2 Discovery of Catalytic Alkylation Reactions of Quinones3 Proposed Redox Chain Reaction Mechanism and Experimental Evidence4 Substrate Scope5 Conclusion