Synthesis of New Rh-Cp Complex with an Ester Group Tethered on the Cp Ring and Its Application in the Catalytic Synthesis of iso-Quinolines

doi:10.6023/cjoc202402014

Abstract

A new type of cyclopentadienyl metal rhodium catalyst was synthesized by introducing an ester functional group onto the cyclopentadienyl group. The catalyst was evaluated with C—H active [4＋2] annulation of aryl oximes and alkynes. The result demonstrated that the new catalyst was superior to conventional catalysts [Cp*RhCl₂]₂ in terms of reactivity and the usage of the metal acetate added.

Key words: iso-quinoline, Rh-Cp complex, [4＋2] annulation, oxime, alkyne

Cite this article

Huan Jin, Yanjun Zhu, Fang Li, Yunfei Luo. Synthesis of New Rh-Cp Complex with an Ester Group Tethered on the Cp Ring and Its Application in the Catalytic Synthesis of iso-Quinolines[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2906-2914.

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Entry	Solvent	Additive	Yield^b/%
1	CH₃OH	Cu(OAc)₂	95
2^c	CH₃OH	Cu(OAc)₂	NR
3	Toluene	Cu(OAc)₂	NR
4	Acetone	Cu(OAc)₂	14
5	DMF	Cu(OAc)₂	10
6	CH₃CN	Cu(OAc)₂	NR
7	THF	Cu(OAc)₂	NR
8	CH₃CH₂OH	Cu(OAc)₂	17
9	CH₃OH	Zn(OAc)₂	23
10	CH₃OH	AgOAc	78
11	CH₃OH	NaOAc	24
12	CH₃OH	KOAc	31
13^d	CH₃OH	Cu(OAc)₂	80
14^e	CH₃OH	Cu(OAc)₂	34
15	CH₃OH	—	30
16^f	CH₃OH	—	NR

Entry	Solvent	Additive	Yield^b/%
1	CH₃OH	Cu(OAc)₂	95
2^c	CH₃OH	Cu(OAc)₂	NR
3	Toluene	Cu(OAc)₂	NR
4	Acetone	Cu(OAc)₂	14
5	DMF	Cu(OAc)₂	10
6	CH₃CN	Cu(OAc)₂	NR
7	THF	Cu(OAc)₂	NR
8	CH₃CH₂OH	Cu(OAc)₂	17
9	CH₃OH	Zn(OAc)₂	23
10	CH₃OH	AgOAc	78
11	CH₃OH	NaOAc	24
12	CH₃OH	KOAc	31
13^d	CH₃OH	Cu(OAc)₂	80
14^e	CH₃OH	Cu(OAc)₂	34
15	CH₃OH	—	30
16^f	CH₃OH	—	NR

Entry	Product	Yield^b/%
Entry	Product	[Cp*RhCl₂]₂	Cp^AcRh(III)
1	3c	59	84
2	3e	71	90
3	3j	63	87
4	3m	54	79

Entry	Product	Yield^b/%
Entry	Product	[Cp*RhCl₂]₂	Cp^AcRh(III)
1	3c	59	84
2	3e	71	90
3	3j	63	87
4	3m	54	79

Entry	Catalyst	Additive	Yield^b/%
1	Cp^AcRh(III) (5 mol%)	—	52
2	Cp^AcRh(III) (10 mol%)	—	73
3	[Cp^*RhCl₂]₂ (5 mol%)	—	Trace
4	Cp^AcRh(III) (2.5 mol%)	Cu(OTf)₂ (5 mol%)	33
5	[Cp^*RhCl₂]₂ (2.5 mol%)	Cu(OTf)₂ (5 mol%)	Trace
6	Cp^AcRh(III) (2.5 mol%)	NaOAc (5 mol%)	80
7	Cp^AcRh(III) (5 mol%)	AgSbF₆ (10 mol%)	51
8	[Cp^*RhCl₂]₂ (2.5 mol%)	AgSbF₆ (10 mol%)	45

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