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Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.012 Å R factor = 0.079 wR factor = 0.192 Data-to-parameter ratio = 15.8For details of how these key indicators were automatically derived from the article, see

A new, efficient and green protocol for the nano-Cu 2 O-catalyzed homo-coupling reaction of terminal alkynes has been developed, using water/ionic liquid as an environmentally friendly solvent. Moreover, the system also allows the synthesis of unsymmetric 1,3-diynes by cross-coupling of two different terminal alkynes. It is noteworthy that the nano-Cu 2 O-catalyzed methodology is a good supplement to copper catalyst for the Glaser-type homo-coupling reaction.Additional supporting information may be found in the online version of this article at the publisher's web site. Scheme 2. Nano-Cu 2 O-catalyzed coupling reaction of 1-ethynylbenzene and 1-ethynyl-4-methoxybenzene.Scheme 3. Possible mechanism for the nano-Cu 2 O-catalyzed coupling reaction of terminal alkyne.

A novel method was developed for Heck reaction of olefins and arylboronic acids using a ligand-free PdCl 2 catalyst to afford the coupling products with excellent regio-and stereoselectivity. It is noteworthy that the PdCl 2 /CuSO 4 /K 2 CO 3 /TBAB/H 2 O system can be recovered and used for three cycles directly.