CuMoO₄ Catalyzed Csp²−Se Cross‐Coupling of Aryl Bromide and Iodide with Diaryldiselenides in Water

Abstract

In this work, an oxo-bridged bimetallic CuMoO 4 catalyst for Csp 2 À Se cross-coupling of diaryldiselenides with aryl-halides is reported. The current discovery is noteworthy, as the catalyst is eco-friendly, easily accessible, air-stable, and recyclable. The methodology exhibits broad substrate scope and the catalytic system tolerates common functional groups.The protocol uses aryl iodide and bromides as electrophile instead of boronic acids. This is the first example of using an oxo-bridged copper based bimetallic catalyst for Csp 2 À Se cross-coupling reactions in water. CÀ Cl bond remains intact during reaction.

t‐BuOH Solvent for CuSeO3CatalyzedCsp2‐SeCross‐coupling of Diaryldiselenide with Arylhalides and Boronic acids

“…The above results inspired us for synthesis of selenoethers by Csp 2 ‐Se cross‐coupling of diarylselenides and aryl halides with CuSeO 3 .2H 2 O catalyst [15] . Our earlier report revealed synthesis of selenoethers using CuMoO 4 −H 2 O‐TBAB system at 100 °C using aryl iodide and bromides with diaryl diselenide [18] . Nonetheless, the present work involves aryl/hetero (aryl) boronic acid as coupling partner in addition to iodides and bromides at low temperature (70 °C) with broad substrate scope (Figure 2).…”

“…[16] The catalyst might be opening the oxo-bridge in presence of diaryl diselenide and t-BuOH to form pre-cursor complex b, which on subsequent reaction with arylhalide and KOH forms complex c. The catalyst is regenerated by reductive elimination and provides selenoether products. [4,[17][18][19] During process from b to c, ArSe À is generated and converted to Ar 2 Se 2 in presence of air.…”

“…[15] Our earlier report revealed synthesis of selenoethers using CuMoO 4 À H 2 O-TBAB ChemistrySelect www.chemistryselect.org system at 100 °C using aryl iodide and bromides with diaryl diselenide. [18] Nonetheless, the present work involves aryl/ hetero (aryl) boronic acid as coupling partner in addition to iodides and bromides at low temperature (70 °C) with broad substrate scope (Figure 2).…”

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

“…[169] An oxo-bridged bimetallic CuMoO 4 catalyst was applied to the Csp 2 À Se crosscoupling of diorganyl diselenides with aryl bromide and iodide in the synthesis of diaryl selenides 117 (Scheme 110). [170] The novelty of this methodology includes easily accessible, airstable, and recyclable catalyzed in addition to the reactions carried out in water. Besides, the reactions showed a high atom economy because only 0.5 equiv.…”