Herein,　we　report　a　nickel-catalyzed　oxidative　coupling　reaction　for　the　synthesis　of　3-azo-substituted　2-oxindoles.　The　key　intermediates　of　3-arylazohexahydropyrrolo-[2,3-b]indoles　undergo　further　transformation　to　provide　3-azo-substituted　2-oxindoles　in　the　presence　of　H2O,　aryldiazonium　tetrafluoroborate　salts　and　catalytic　amount　of　NiBr2.　This　reaction　can　be　performed　in　an　open　flask　at　room　temperature　and　exhibits　a　broad　functional-group　tolerance　in　moderate　to　excellent　yields.