Palladium-Catalyzed C(sp3)—Si Bonds Transformation for Construct-ing Trifluoropropyl (Hetero)arenes through C(sp3)—C(sp2) Cross-Coupling Reactions

doi:10.6023/cjoc202310013

Abstract

Palladium-catalyzed C(sp³)—Si bonds transformation of commercially available polyalkoxy trifluorosilane reagents has been developed through C(sp³)—C(sp²) cross-coupling reactions. This Hiyama cross-coupling reaction shows good functional group tolerance and provides a series of trifluoropropyl (hetero)arenes. The fluoride source and alkyl tether of bisphosphine ligand play important roles in improving yields.

Key words: palladium catalysis, Hiyama cross-coupling reaction, fluoroalkylation, organosilicon

Cite this article

Junjun Liu, Taotao Lu, Ping Ma, Qingyang Zhao, Fuk Yee Kwong. Palladium-Catalyzed C(sp³)—Si Bonds Transformation for Construct-ing Trifluoropropyl (Hetero)arenes through C(sp³)—C(sp²) Cross-Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1319-1326.

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Fig. & Tab. 5

References 21

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Entry	L	[Pd]	F^– source	Solvent	Temp./℃	Yield^b/%
1^c	PPh₃	Pd(OAc)₂	TBAF	THF	100	36
2^c	PCy₃	Pd(OAc)₂	TBAF	THF	100	42
3^c	XPhos	Pd(OAc)₂	TBAF	THF	100	15
4	dppm	Pd(OAc)₂	TBAF	THF	100	49
5	dppe	Pd(OAc)₂	TBAF	THF	100	24
6	dppp	Pd(OAc)₂	TBAF	THF	100	42
7	dppb	Pd(OAc)₂	TBAF	THF	100	48
8	dppP	Pd(OAc)₂	TBAF	THF	100	48
9	dpph	Pd(OAc)₂	TBAF	THF	100	52
10	dppB	Pd(OAc)₂	TBAF	THF	100	17
11	DPEPhos	Pd(OAc)₂	TBAF	THF	100	35
12	dppf	Pd(OAc)₂	TBAF	THF	100	23
13	dpph	PdCl₂	TBAF	THF	100	45
14	dpph	Pd₂(dba)₃	TBAF	THF	100	<5
15	dpph	[Pd(cinnamyl)Cl]₂	TBAF	THF	100	<5
16	dpph	Pd(OTF)₂	TBAF	THF	100	50
17	dpph	Pd(OAc)₂	TBAF	Tol	100	49
18	dpph	Pd(OAc)₂	TBAF	Dioxane	100	41
19	dpph	Pd(OAc)₂	TBAF	MeCN	100	18
20	dpph	Pd(OAc)₂	TBAF	DMF	100	35
21	dpph	Pd(OAc)₂	CsF	THF	100	<5
22	dpph	Pd(OAc)₂	RbF	THF	100	ND
23	dpph	Pd(OAc)₂	KF	THF	100	ND
24^d	dpph	Pd(OAc)₂	TBAF	THF	100	62 (57)
25^e	dpph	Pd(OAc)₂	TBAF	THF	100	46
26 ^d	dpph	Pd(OAc)₂	TBAF	THF	90	57
27 ^d	dpph	Pd(OAc)₂	TBAF	THF	110	62
28 ^d	dpph	Pd(OAc)₂	TBAF	THF	120	53

Entry	L	[Pd]	F^– source	Solvent	Temp./℃	Yield^b/%
1^c	PPh₃	Pd(OAc)₂	TBAF	THF	100	36
2^c	PCy₃	Pd(OAc)₂	TBAF	THF	100	42
3^c	XPhos	Pd(OAc)₂	TBAF	THF	100	15
4	dppm	Pd(OAc)₂	TBAF	THF	100	49
5	dppe	Pd(OAc)₂	TBAF	THF	100	24
6	dppp	Pd(OAc)₂	TBAF	THF	100	42
7	dppb	Pd(OAc)₂	TBAF	THF	100	48
8	dppP	Pd(OAc)₂	TBAF	THF	100	48
9	dpph	Pd(OAc)₂	TBAF	THF	100	52
10	dppB	Pd(OAc)₂	TBAF	THF	100	17
11	DPEPhos	Pd(OAc)₂	TBAF	THF	100	35
12	dppf	Pd(OAc)₂	TBAF	THF	100	23
13	dpph	PdCl₂	TBAF	THF	100	45
14	dpph	Pd₂(dba)₃	TBAF	THF	100	<5
15	dpph	[Pd(cinnamyl)Cl]₂	TBAF	THF	100	<5
16	dpph	Pd(OTF)₂	TBAF	THF	100	50
17	dpph	Pd(OAc)₂	TBAF	Tol	100	49
18	dpph	Pd(OAc)₂	TBAF	Dioxane	100	41
19	dpph	Pd(OAc)₂	TBAF	MeCN	100	18
20	dpph	Pd(OAc)₂	TBAF	DMF	100	35
21	dpph	Pd(OAc)₂	CsF	THF	100	<5
22	dpph	Pd(OAc)₂	RbF	THF	100	ND
23	dpph	Pd(OAc)₂	KF	THF	100	ND
24^d	dpph	Pd(OAc)₂	TBAF	THF	100	62 (57)
25^e	dpph	Pd(OAc)₂	TBAF	THF	100	46
26 ^d	dpph	Pd(OAc)₂	TBAF	THF	90	57
27 ^d	dpph	Pd(OAc)₂	TBAF	THF	110	62
28 ^d	dpph	Pd(OAc)₂	TBAF	THF	120	53

Entry	R—X	[Pd-L]/mol%	Yield^b/%
1	2a'	5	70%
2	2c'	5	<5%
3	2c'	10	11

Entry	R—X	[Pd-L]/mol%	Yield^b/%
1	2a'	5	70%
2	2c'	5	<5%
3	2c'	10	11

钯催化的碳(sp³)-硅键转化实现碳(sp³)-碳(sp²)偶联制备三氟丙基(杂)芳烃

Palladium-Catalyzed C(sp³)—Si Bonds Transformation for Construct-ing Trifluoropropyl (Hetero)arenes through C(sp³)—C(sp²) Cross-Coupling Reactions

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钯催化的碳(sp3)-硅键转化实现碳(sp3)-碳(sp2)偶联制备三氟丙基(杂)芳烃