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. 2018 Dec 4;8(70):40446-40453.
doi: 10.1039/c8ra06938g. eCollection 2018 Nov 28.

A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes

Raju Jannapu Reddy  1 , Md Waheed  1 , Jangam Jagadesh Kumar  1
Affiliations

A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes

Raju Jannapu Reddy et al. RSC Adv. .

Abstract

A practical, highly flexible and eco-friendly method has been developed for the synthesis of allyl thiosulfonates using Morita-Baylis-Hillman (MBH) allyl bromides and sodium arylthiosulfonates, which were readily assembled without any reagent/catalyst. Moreover, the allyl thiosulfonates were successfully transformed into a set of two synthetically viable diallyl disulfanes and unsymmetrical allyl disulfanes in the presence of Cs2CO3. The present protocols are operationally simple and convenient to generate a wide range of functionalized allyl thiosulfonates and allyl disulfanes in good to excellent yields.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Strategy for synthesis of allyl thiosulfonates and allyl disulfanes.
Scheme 2
Scheme 2. Synthesis of methyl 2H-thiochromene-3-carboxylate (4).
Scheme 3
Scheme 3. Reactions performed on 0.8 mmol of 3ab/3hb with KSAc (1.5 eq.). A gram scale reaction of allyl bromide 1a with 2b/KSAc for the synthesis of 7a.
Scheme 4
Scheme 4. Control experiments.
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