Aerobic Construction of 2-Acyl Benzoxazole by Tandem C—H Oxygenation and Oxazole Ring Formation

doi:10.6023/cjoc202109029

Abstract

The synthesis of useful 2-acyl benzoxazoles has been realized via the tandem methylene C—H oxygenation and oxazole annulation of N-(o-hydroxyphenyl)phenylacetamides via copper catalysis in one-pot fashion. Besides featuring the incomparable step-economy resulting from the multi-step transformation, the tunable synthesis of diverse 2-methylene functionalized benzoxazoles using identical starting materials as well as the expanded synthesis of corresponding benzothiazoles is also attractive advantage of the work.

Key words: tandem, C—H oxygenation, annulation, 2-acyl benzoxazole, selectivity

Cite this article

Zhi Tu, Baoli Zhao, Jieping Wan, Chaoli Wang, Yunyun Liu. Aerobic Construction of 2-Acyl Benzoxazole by Tandem C—H Oxygenation and Oxazole Ring Formation[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4780-4788.

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Entry	Catalyst	Solvent	Yield/% of 2a	Yield/% of 3a
1	—	AcOH	27	49
2	—	DMSO	0	Trace
3	—	DMF	0	Trace
4	—	EtOH	0	15
5	—	Toluene	0	0
6	CuSO₄	AcOH	45	37
7	Cu(OAc)₂	AcOH	74	11
8	CuI	AcOH	77	Trace
9	CuBr	AcOH	80	Trace
10^c	CuBr	AcOH	69	18
11^d	CuBr	AcOH	78	Trace
12^e	CuBr	AcOH	78	Trace
13^d^,^f	CuBr	AcOH	56	17
14^d^,^g	CuBr	AcOH	75	Trace
15	p-TSA	AcOH	Trace	74
16^h	p-TSA	AcOH	Trace	76
17ⁱ	p-TSA	AcOH	Trace	80
18^j	p-TSA	AcOH	Trace	79
19^d^,^k	CuBr	AcOH	11	59
20^d^,^l	CuBr	AcOH	77	Trace

Entry	Catalyst	Solvent	Yield/% of 2a	Yield/% of 3a
1	—	AcOH	27	49
2	—	DMSO	0	Trace
3	—	DMF	0	Trace
4	—	EtOH	0	15
5	—	Toluene	0	0
6	CuSO₄	AcOH	45	37
7	Cu(OAc)₂	AcOH	74	11
8	CuI	AcOH	77	Trace
9	CuBr	AcOH	80	Trace
10^c	CuBr	AcOH	69	18
11^d	CuBr	AcOH	78	Trace
12^e	CuBr	AcOH	78	Trace
13^d^,^f	CuBr	AcOH	56	17
14^d^,^g	CuBr	AcOH	75	Trace
15	p-TSA	AcOH	Trace	74
16^h	p-TSA	AcOH	Trace	76
17ⁱ	p-TSA	AcOH	Trace	80
18^j	p-TSA	AcOH	Trace	79
19^d^,^k	CuBr	AcOH	11	59
20^d^,^l	CuBr	AcOH	77	Trace

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