The synthesis of 1,2-diferrocenylethanedione (II) was achieved through metal-free route. Tröger's-base functionalized pre-N-heterocyclic carbenes, TB-[CH 2-Im-CH 2-Mes] 2 +2X, where TB = 6H,12H-5,11-methano-dibenzo[b,f][1,5]diazocine; Im = imidazolium; Mes = 2,4,6-trimethylbenzene; X = Br (4), BF 4 (5) and PF 6 (6) were synthesized in very good yield through simple synthetic route. 4-6 were characterized by FT-IR and multinuclear NMR. These new molecules, 4-6 were used as an organocatalyst to study the ferrocenealdehyde condensation reactions. 4-6 mediated condensation of ferrocenealdehyde resulted the mixture of 2-hydroxy-1,2-diferrocenyl-ethan-1-one (major product, I) to 1,2-diferrocenylethanedione (minor product, II). II was conveniently separated from reaction mixture by hexane wash, while the purification of I using silica loaded column chromatography resulted the quantitative oxidation of I to II. Catalysts [{2,6-Me 2C 6H 3N(CH) 2N(CH 2Mes)}CH] +Br - (7) and [{CH 2CHN(CH) 2N(CH 2Mes)}CH] +Br - (8) as well as 7-8 in the presence of 2,8-dibromo tröger base also showed similar catalytic behavior, however yield of II was very poor. Among 4-8, catalyst 4 in THF gave the best conversion. © 2012 Elsevier B.V. All rights reserved.