Gold‐Catalyzed Synthesis of Iodofulvenes

Abstract

We report the gold-catalyzed synthesis of highly functionalized iodofulvenes from iododialkynes under mild conditions. The catalytic cycle involves the formation of gold acetylides and vinylgold intermediates. These intermediates can then undergo an unprecedented iodine/gold exchange. This new pathway for catalyst transfer in dual gold catalysis opens up the possibility of highly regioselective transformations directed by the gold in the organogold intermediates. The resulting products are well suited for further metal-mediated coupling reactions, allowing the synthesis of extended π-systems.

Intriguing mechanistic labyrinths in gold(i) catalysis

“…129 It is interesting that, in contrast to that found in the reactions between alkynes and alkenes, these types of diyne cyclizations are smoothly catalysed with σ,π-digold( i ) alkyne complexes. 129–131 …”

New Pathways for the Dual Gold‐Catalyzed Cyclization of Diynes

“…Gold catalysis has emerged as ah ighly active field in homogenous catalysis in recent decades. [1] Recently, Zhang's group and our group independently discovered an ew reactivity pattern for gold-catalyzedr eactions, in the course of the studies onto the activation of diynes, [2,3] which was entitled"dual activation". This termw as first introduced by To stee tal.…”

Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

“…Recent studies have provided strong evidence for their existence, and have demonstrated their powerful reactivity [51–55], identifying them as key players in ongoing activity developing the exciting notion of dual activation using gold catalysts [56]. …”