. Author manuscript; available in PMC: 2023 May 11.

Published in final edited form as: J Am Chem Soc. 2022 May 2;144(18):8242–8248. doi: 10.1021/jacs.2c01487

Table 1.

Discovery and control experiments for organophosphorus-catalyzed C(sp²)–N cross coupling with nitroalkane 1.^a



Entry	P•[O]	Deviation from sth. cond.	Yield (%)^b

1	P1•[O]	in CPME (0.5 M) w/o MgO	10
2	P1•[O]	--	24
3	P2•[O]	--	73
4	P3•[O]	--	69
5	P4•[O]	--	90
6	none	--	0
7	P4•[O]	omit hydrosilane	0

Reactions were carried out with P4•[O] (0.027 mmol, 15 mol %), diphenylsilane (0.730 mmol, 4.0 equiv), boronic acid 2 (0.274 mmol, 1.5 equiv) and nitroalkane 1 (0.182 mmol, 1.0 equiv) in CPME:PivCN = 6:4 (0.3 M) at 120 °C for 24 h, unless noted otherwise.

Yields were determined by ¹H NMR integration with the aid of an internal standard.

The energy gap of HOMO-LUMO was measured from P(III) state.