镍催化1,6-烯炔与芳基卤化物的反式还原芳基化环化

doi:10.6023/cjoc202401001

有机化学 ›› 2024, Vol. 44 ›› Issue (6): 1938-1948.DOI: 10.6023/cjoc202401001 上一篇下一篇

研究论文

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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摘要/Abstract

发展了一种镍催化1,6-烯炔与芳基卤化物的反式还原芳基化环化反应. 该反应避免了化学计量有机金属试剂的使用, 而且条件温和、官能团兼容性好、底物范围广. 许多天然产物和生物活性化合物中广泛存在各种碳环和杂环骨架, 该方法为这些骨架的合成提供了一个高效的平台.

关键词: 镍催化, 还原偶联, 1,6-烯炔, 串联环化

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

引用此文

邢运新, 闫登鸿, 温顺, 卜洁, 沈坤. 镍催化1,6-烯炔与芳基卤化物的反式还原芳基化环化[J]. 有机化学, 2024, 44(6): 1938-1948.

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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图/表 6

Scheme 1. Transition metal-catalyzed arylative cyclization of 1,6-enynes

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

Table 1. Reaction condition optimizationa

Table 2. Reaction scope of aryl halidesa

Table 3. Reaction scope of 1,6-enynesa

Scheme 2. Further studies on the reaction scope of 1,6-enynes

Scheme 4. Proposed mechanism

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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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