Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds

doi:10.6023/cjoc202304003

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4227-4238.DOI: 10.6023/cjoc202304003 Previous Articles Next Articles

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锡粉促进下1,3-二取代-1,3-二氢异苯并呋喃化合物的合成

唐朵朵, 黄丹凤^*(), 王克虎, 马虎, 冯杨, 任园园, 王君姣, 胡雨来

西北师范大学化学化工学院兰州 730070

收稿日期:2023-04-04 修回日期:2023-06-05 发布日期:2023-08-16
基金资助:
国家自然科学基金(21861033); 国家自然科学基金(22061037)

Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds

Duoduo Tang, Danfeng Huang^*(), Kehu Wang, Hu Ma, Yang Feng, Yuanyuan Ren, Junjiao Wang, Yulai Hu

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2023-04-04 Revised:2023-06-05 Published:2023-08-16
Contact: *E-mail: huangdf@nwnu.edu.cn
Supported by:
National Natural Science Foundation of China(21861033); National Natural Science Foundation of China(22061037)

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Abstract

An efficient approach for the construction of 1,3-disubstituted-1,3-dihydroisobenzofuran compounds was developed through tin powder mediated tandem allylation/oxa-Michael addition reaction of o-formyl chalcones with various allyl bromides under mild reaction conditions. This method is easy to operate and can tolerate various functional groups to give the corresponding 1,3-disubstituted-1,3-dihydroisobenzofuran compounds in good to excellent yields.

Key words: tin powder, allyl bromide, o-formyl chalcone, 1,3-dihydroisobenzofuran

Cite this article

Duoduo Tang, Danfeng Huang, Kehu Wang, Hu Ma, Yang Feng, Yuanyuan Ren, Junjiao Wang, Yulai Hu. Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4227-4238.

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Fig. & Tab. 6

References 27

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Entry	Molar ratio of 1a∶2a∶Sn	Additive (equiv.)	Solvent	Time^b/h	Yield^c/%	cis∶trans^d^[5]
1	1.0∶2.0∶2.5	None	THF	12	66	1.0∶2.4
2	1.0∶3.0∶3.5	None	THF	12	56	1.0∶1.0
3	1.0∶1.0∶1.5	None	THF	9	54	1.0∶1.2
4	1.0∶2.0∶2.5	In(OTf)₃ (0.2)	THF	6	50	2.2∶1.0
5	1.0∶2.0∶2.5	AgOTf (0.2)	THF	12	67	1.0∶2.0
6	1.0∶2.0∶2.5	Fe(OTf)₃ (0.2)	THF	7	69	1.0∶1.5
7	1.0∶2.0∶2.5	BF₃•Et₂O (0.2)	THF	8	58	1.6∶1.0
8	1.0∶2.0∶2.5	TsOH (0.2)	THF	8	63	1.1∶1.0
9	1.0∶2.0∶2.5	TfOH (0.2)	THF	8	54	1.0∶1.0
10	1.0∶2.0∶2.5	H₃PO₄ (0.2)	THF	9	36	1.3∶1.0
11	1.0∶2.0∶2.5	HCl (0.2)	THF	9	67	1.0∶1.0
12	1.0∶2.0∶2.5	HClO₄ (0.2)	THF	5	70	1.0∶1.2
13	1.0∶2.0∶2.5	HClO₄ (0.5)	THF	4	78	1.4∶1.0
14	1.0∶2.0∶2.5	HClO₄ (1)	THF	3	53	1.8∶1.0
15	1.0∶2.0∶2.5	HClO₄ (0.5)	Dioxane	1	58	1.2∶1.0
16	1.0∶2.0∶2.5	HClO₄(0.5)	DCM	14	30	1.0∶1.8
17	1.0∶2.0∶2.5	HClO₄ (0.5)	Toluene	1	—	—
18	1.0∶2.0∶2.5	HClO₄ (0.5)	CH₃CN	1	53	1.0∶1.0
19	1.0∶2.0∶2.5	HClO₄ (0.5)	EtOH	1	83	1.0∶1.1

Entry	Molar ratio of 1a∶2a∶Sn	Additive (equiv.)	Solvent	Time^b/h	Yield^c/%	cis∶trans^d^[5]
1	1.0∶2.0∶2.5	None	THF	12	66	1.0∶2.4
2	1.0∶3.0∶3.5	None	THF	12	56	1.0∶1.0
3	1.0∶1.0∶1.5	None	THF	9	54	1.0∶1.2
4	1.0∶2.0∶2.5	In(OTf)₃ (0.2)	THF	6	50	2.2∶1.0
5	1.0∶2.0∶2.5	AgOTf (0.2)	THF	12	67	1.0∶2.0
6	1.0∶2.0∶2.5	Fe(OTf)₃ (0.2)	THF	7	69	1.0∶1.5
7	1.0∶2.0∶2.5	BF₃•Et₂O (0.2)	THF	8	58	1.6∶1.0
8	1.0∶2.0∶2.5	TsOH (0.2)	THF	8	63	1.1∶1.0
9	1.0∶2.0∶2.5	TfOH (0.2)	THF	8	54	1.0∶1.0
10	1.0∶2.0∶2.5	H₃PO₄ (0.2)	THF	9	36	1.3∶1.0
11	1.0∶2.0∶2.5	HCl (0.2)	THF	9	67	1.0∶1.0
12	1.0∶2.0∶2.5	HClO₄ (0.2)	THF	5	70	1.0∶1.2
13	1.0∶2.0∶2.5	HClO₄ (0.5)	THF	4	78	1.4∶1.0
14	1.0∶2.0∶2.5	HClO₄ (1)	THF	3	53	1.8∶1.0
15	1.0∶2.0∶2.5	HClO₄ (0.5)	Dioxane	1	58	1.2∶1.0
16	1.0∶2.0∶2.5	HClO₄(0.5)	DCM	14	30	1.0∶1.8
17	1.0∶2.0∶2.5	HClO₄ (0.5)	Toluene	1	—	—
18	1.0∶2.0∶2.5	HClO₄ (0.5)	CH₃CN	1	53	1.0∶1.0
19	1.0∶2.0∶2.5	HClO₄ (0.5)	EtOH	1	83	1.0∶1.1

锡粉促进下1,3-二取代-1,3-二氢异苯并呋喃化合物的合成

Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds

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