Nature Communications

Table 1 The effects of different reaction conditions

From: Selective nitrogen insertion into aryl alkanes


Entry	Oxidant	Reductant	Solvent	Yield^a (%)
1	DDQ	NaBH₃CN	HFIP	98
2	1,4-benzoquinone	NaBH₃CN	HFIP	26
3	Chloranil	NaBH₃CN	HFIP	40
4	H₂O₂	NaBH₃CN	HFIP	N.R.
5	DDQ	NaBH₄	HFIP	80
6	DDQ	HBpin	HFIP	91
7	DDQ	NaBH₃CN	CF₃CH₂OH	95
8	DDQ	NaBH₃CN	ⁱPrOH	41
9	DDQ	NaBH₃CN	THF	41
10	DDQ	NaBH₃CN	DCM	88
11	DDQ	NaBH₃CN	DMSO	N.R.
12^b	DDQ	NaBH₃CN	HFIP	96
13^c	DDQ	NaBH₃CN	HFIP	57
14^d	DDQ	NaBH₃CN	HFIP	88
15	–	NaBH₃CN	HFIP	N.R.
16	DDQ	–	HFIP	N.R.

^aGeneral reaction conditions: 1 (0.3 mmol), 2 (0.45 mmol), DDQ (0.45 mmol), H₂O (3.0 mmol), HFIP (1.5 mL), N₂, 25 °C, 12 h, then NaBH₃CN (1.5 mmol), 2 h. Isolated yield.
^b60 °C instead of 25 °C.
^c0 °C instead of 25 °C.
^dNo water.

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