Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides

doi:10.6023/cjoc202401001

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1938-1948.DOI: 10.6023/cjoc202401001 Previous Articles Next Articles

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镍催化1,6-烯炔与芳基卤化物的反式还原芳基化环化

邢运新, 闫登鸿, 温顺, 卜洁, 沈坤^*()

武汉大学药学院武汉 430071

收稿日期:2024-01-01 修回日期:2024-02-07 发布日期:2024-03-05
基金资助:
国家自然科学基金(21901192); 国家自然科学基金(22271225); 湖北省自然科学基金(2019CFB12); 湖北省自然科学基金(2022CFB221)

Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides

Yunxin Xing, Denghong Yan, Shun Wen, Jie Bu, Kun Shen^*()

School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071

Received:2024-01-01 Revised:2024-02-07 Published:2024-03-05
Contact: * E-mail: kun.shen@whu.edu.cn
Supported by:
National Natural Science Foundation of China(21901192); National Natural Science Foundation of China(22271225); Natural Science Foundation of Hubei Province(2019CFB12); Natural Science Foundation of Hubei Province(2022CFB221)

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Abstract

A nickel-catalyzed reductive trans-arylative cyclization of 1,6-enynes with aryl halides has been developed. This transformation avoids the use of stoichiometric organometallic reagents and features mild conditions, good functional group tolerance and broad substrate scope. This method serves as an efficient platform for the synthesis of various carbo- and heterocycles, which are abundant in many natural products and biologically active compounds.

Key words: nickel catalysis, reductive cross-coupling, 1,6-enyne, tandem cyclization

Cite this article

Yunxin Xing, Denghong Yan, Shun Wen, Jie Bu, Kun Shen. Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1938-1948.

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Fig. & Tab. 6

References 14

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Entry	Variation	Yield^b/%
1	No variation	76 (71)
2	L2 instead of L1	48
3	L3 instead of L1	59
4	L4 instead of L1	66
5	L5 instead of L1	34
6	L6 instead of L1	0
7	Zn instead of Mn	42
8	No ligand	0
9	No Mn	0
10	60 ℃ instead of 80 ℃	67
11	1a' instead of 1a	0
12	Phenyl bromide instead of 2a	59

Entry	Variation	Yield^b/%
1	No variation	76 (71)
2	L2 instead of L1	48
3	L3 instead of L1	59
4	L4 instead of L1	66
5	L5 instead of L1	34
6	L6 instead of L1	0
7	Zn instead of Mn	42
8	No ligand	0
9	No Mn	0
10	60 ℃ instead of 80 ℃	67
11	1a' instead of 1a	0
12	Phenyl bromide instead of 2a	59

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镍催化1,6-烯炔与芳基卤化物的反式还原芳基化环化

Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides

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