Reported　herein　is　the　design　of　a　new　catalytic　paradigm　by　synergistically　combining　sequential　paired　electrosynthesis　with　halogen-bonding　(XB)　activation　for　the　cyclization　of　organochlorides　with　olefins.　This　dual　activation　strategy　enables　rapid　access　to　densely　functionalized　2-alkylidene-tetrahydrofurans　with　exclusive　Z-selectivities,　which　are　challenging　to　be　synthesized　by　other　methods.　4,4＇-Di-tert-butyl-2,2＇-bipyridine　(dtbbpy)　showed　an　unprecedented　reactivity　as　a　XB　acceptor　to　activate　C-Cl　bond　by　shifting　its　reduction　potential　positively　by　220　mV.　Distinctly　different　from　previous　electroreductions　of　C-Cl　bonds　relying　upon　high　electrode　potentials　or　matched　redox　properties　between　mediators　and　organochlorides,　the　XB　activator　employed　herein　has　no　limit　on　the　abovementioned　redox　property　matching　but　can　lower　the　applied　electrode　potentials.　The　decreased　operating　potential　allows　broad　functional　group　tolerance,　which　was　highlighted　by　the　late-stage　functionalization　of　11　examples　of　drugs　and　natural　products-derived　alkenes.