. Author manuscript; available in PMC: 2013 Sep 12.

Published in final edited form as: J Am Chem Soc. 2012 Sep 4;134(36):15154–15162. doi: 10.1021/ja3075924

Table 2.

Pyridine yields and product ratios from stoichiometric cross-cycloaddition reactions^a,^b

entry	dimer 3	R₂CN (equiv)	yield of 5 (R₁:R₂)	post-reaction dimer species
1	3a	PhCN(1)	84% (1:27)	3a
2	3b	MeCN (1)	74% (1:1.6)	3b
3	3b	MeCN (10)	67% (1:2.9)	3b/3a^c
4	3b	4-CF₃-C₆H₄ (1)	93% (1:4.5)	3b/3d^c
5	3b	4-MeO-C₆H₄ (1)	95% (1:4)	3b
6	3c	MeCN (1)	63% (1:1.4)	3c^c
7	3c	MeCN (10)	91% (1:1.9)	3c^c,^d
8	3c	PhCN (1)	96% (1:4.3)	3c^c
9	3d	MeCN (1)	69% (1:2.1)	3d
10	3d	PhCN (1)	99% (1:11)	3d

Dimer 3 (1 equiv), diyne 4 (1 equiv), nitrile (1 equiv), C₆D₆, 23 °C.

Yields, product ratios, and post-reaction dimer species determined by ¹H NMR spectroscopy with ferrocene as an internal standard.

Traces of unknown Ni species were detected.

Complex mixture of Ni products were formed.