A new electrochemical three-component annulation−iodosulfonylation of 1,5-enyne-containing para-quinone methides (p-QMs) has been established by using available arylsulfonyl hydrazides and potassium iodide under environmentally benign conditions. The electrosynthesis offers sustainable and efficient access to construct spirocyclohexadienone-containing (E)indenes without any additional catalyst or oxidant through a sulfonyl-radical-triggered 1,6-addition and an I + -mediated ipsocyclization cascade. Notably, potassium iodide plays the triple role of an electrolyte, a redox catalyst, as well as an iodination reagent.
A visible light photocatalytic methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes has been established using a dimethyl sulfoxide (DMSO)/H2O system as the methylsulfonyl source.
A new Pd(II)-catalyzed carbonyl-directing activation of alkenes has been established, enabling radical-induced selective fluorosulfonylation and aminosulfonylation of carbonyl-tethered 1,7-enynes with sulfinic acids and N-fluorobenzenesulfonimide (NFSI) under mild and redox neutral conditions to access densely functionalized ( E)-3,4-dihydronaphthalen-1(2 H)-ones with generally good yields and high stereoselectivity. The selectivity of these bifunctionalizations relies on the electronic nature of substituents on both aryl rings of 1,7-enynes.
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