α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents

doi:10.6023/cjoc202205031

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3766-3775.DOI: 10.6023/cjoc202205031 Previous Articles Next Articles

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环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应

高珠鹏^a, 项锴^b, 徐学涛^c^,^*(), 张雅婷^a, 朱道勇^a^,^*()

^a兰州大学药学院兰州 730000
^b北京航天试验技术研究所北京 100074
^c五邑大学生物科技与大健康学院广东江门 529020

收稿日期:2022-05-18 修回日期:2022-06-30 发布日期:2022-07-20
通讯作者: 徐学涛, 朱道勇
基金资助:
广东省教育厅(2017KTSCX185); 广东省教育厅(2017KSYS010); 广东省教育厅(2019KZDXM035); 甘肃省科技计划(20JR10RA608)

α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents

Zhupeng Gao^a, Kai Xiang^b, Xuetao Xu^c(), Yating Zhang^a, Daoyong Zhu^a()

^aSchool of Pharmacy, Lanzhou University, Lanzhou 730000
^bBeijing Institute of Aerospace Testing Technology, Beijing 100074
^cSchool of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020

Received:2022-05-18 Revised:2022-06-30 Published:2022-07-20
Contact: Xuetao Xu, Daoyong Zhu
Supported by:
Department of Education of Guangdong Province(2017KTSCX185); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2019KZDXM035); Science and Technology Program of Gansu Province(20JR10RA608)

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Abstract

A one-pot method for the α-benzoyloxylation of β-dicarbonyl compounds using trivalent iodine reagent was developed. The success of this protocol hinges on the the in situ generation of silylenol ether structure followed by electrical property-promoted reductive rearrangement of a umpolung intermediate. This reaction has good atomic economy, which is not only suitable for gram scale preparation and subsequent derivatization applications, but also expands the application range of cyclic trivalent iodine and its derivatives in the field of polarity reversal.

Key words: trivalent iodine reagent, β-dicarbonyl compound, α-benzoyloxylation, umpolung

Cite this article

Zhupeng Gao, Kai Xiang, Xuetao Xu, Yating Zhang, Daoyong Zhu. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3766-3775.

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Entry	Solvent	Temperature	Et₃N (equiv.)	3aa^b/%
1	CH₂Cl₂	－78 ℃ to r.t.	1.3	n.d.^c^,^d
2	CH₂Cl₂	－78 ℃ to r.t.	1.3	60
3	CH₂Cl₂	－78 ℃ to r.t.	1.5	40
4	CH₂Cl₂	－78 ℃ to r.t.	1.7	30
5	CH₂Cl₂	－78 ℃ to r.t.	2.1	30
6	CH₂Cl₂	－78 ℃ to r.t.	2.3	20
7	THF	－78 ℃ to r.t.	1.3	Trace
8	Cyclohexane	－78 ℃ to r.t.	1.3	57
9	n-Heptane	－78 ℃ to r.t.	1.3	61
10	toluene	－78 ℃ to r.t.	1.3	60
11	n-Hexane	－78 ℃ to r.t.	1.3	67
12	n-Hexane	－78 ℃ to r.t.	1.0	29
13	n-Hexane	－78 ℃ to r.t.	1.1	34
14	n-Hexane	－78 ℃ to r.t.	1.5	52
15	n-Hexane	－78 ℃ to r.t.	1.7	56
16	n-Hexane	－78 ℃ to r.t.	2.0	69
17	n-Hexane	－78 ℃ to r.t.	2.2	24
18	n-Hexane	－60 ℃ to r.t.	2.0	66
19	n-Hexane	－40 ℃ to r.t.	2.0	73
20	n-Hexane	－20 ℃ to r.t.	2.0	64
21	n-Hexane	0 ℃ to r.t.	2.0	52
22	n-Hexane	60 ℃	2.0	70
23	n-Hexane	70 ℃	2.0	61

Entry	Solvent	Temperature	Et₃N (equiv.)	3aa^b/%
1	CH₂Cl₂	－78 ℃ to r.t.	1.3	n.d.^c^,^d
2	CH₂Cl₂	－78 ℃ to r.t.	1.3	60
3	CH₂Cl₂	－78 ℃ to r.t.	1.5	40
4	CH₂Cl₂	－78 ℃ to r.t.	1.7	30
5	CH₂Cl₂	－78 ℃ to r.t.	2.1	30
6	CH₂Cl₂	－78 ℃ to r.t.	2.3	20
7	THF	－78 ℃ to r.t.	1.3	Trace
8	Cyclohexane	－78 ℃ to r.t.	1.3	57
9	n-Heptane	－78 ℃ to r.t.	1.3	61
10	toluene	－78 ℃ to r.t.	1.3	60
11	n-Hexane	－78 ℃ to r.t.	1.3	67
12	n-Hexane	－78 ℃ to r.t.	1.0	29
13	n-Hexane	－78 ℃ to r.t.	1.1	34
14	n-Hexane	－78 ℃ to r.t.	1.5	52
15	n-Hexane	－78 ℃ to r.t.	1.7	56
16	n-Hexane	－78 ℃ to r.t.	2.0	69
17	n-Hexane	－78 ℃ to r.t.	2.2	24
18	n-Hexane	－60 ℃ to r.t.	2.0	66
19	n-Hexane	－40 ℃ to r.t.	2.0	73
20	n-Hexane	－20 ℃ to r.t.	2.0	64
21	n-Hexane	0 ℃ to r.t.	2.0	52
22	n-Hexane	60 ℃	2.0	70
23	n-Hexane	70 ℃	2.0	61

环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应

α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents

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