Table 1.

Discovery and Optimization of Organophosphorus-Catalyzed N–N cross coupling.^a

Entry	Change from “standard conditions”	Yield (%)a
1	none	86 (81)
2	1 (15 mol%)	86
3	1·[O] (5 mol%)	84b
4	no catalyst 1·[O]	0
5	no silane	0
6	no 2,4,6-trimethylbenzoic acid	trace
7	under ambient air	82
8	100 °C	79
9	THF (0.5 M)	41

^aYields were determined through ¹⁹F NMR with 4-fluorotoluene as an internal standard.

^b72 h reaction time. See Supporting Information for full synthetic details.