导向碳氢键活化与不饱和分子的电氧化环化反应

doi:10.6023/cjoc202110028

摘要/Abstract

过渡金属催化导向碳氢键活化与不饱和分子的环化反应已成为合成复杂碳环和杂环化合物的高效途径, 但反应中往往需要额外加入化学计量化学氧化剂来实现反应循环. 电化学有机合成可利用电流代替昂贵、有毒的化学氧化剂, 是一种环境友好的绿色合成手段. 近年来, 电化学有机合成与过渡金属(如Pd、Ni、Co、Ru、Cu、Rh、Ir等)催化碳氢键活化的结合取得了显著的进展. 重点介绍了过渡金属催化导向C—H活化与炔烃、烯烃、一氧化碳和异氰等不饱和分子的电氧化环化反应的最新进展, 并对该领域未来发展方向进行了展望.

关键词: 碳氢键活化, 电氧化, 环化, 不饱和分子

Transition-metal catalyzed directed C—H bond activation and cyclization of unsaturated molecules have been developed as an efficient method to synthesize complex carbon aromatic and heteroaromatic compounds. However, additional stoichiometric oxidants are often required to realize the reoxidation cycle. Electrochemical organic synthesis can use current to replace expensive and toxic oxidants. It is an environment-friendly synthesis method. In recent years, remarkable progress has been made in the combination of electrochemical organic synthesis and C—H activation catalyzed by transition metals (such as Pd, Ni, Co, Ru, Cu, Rh, Ir, etc.). The latest progress of transition-metal catalyzed electrooxidative annulation of unsaturated molecules such as alkynes, olefins, carbon monoxide and isocyanogens via directed C—H activation is reviewed. Finally, the challenges and the future development on this important area are also described.

Key words: C—H bond activation, electrooxidation, cyclization, unsaturated molecule

引用此文

谢吴成, 陈浒, 黎韵越, 林洁玲, 陈婉雯, 石君君. 导向碳氢键活化与不饱和分子的电氧化环化反应[J]. 有机化学, 2022, 42(5): 1286-1306.

Wucheng Xie, Xu Chen, Yunyue Li, Jieling Lin, Wanwen Chen, Junjun Shi. Electrooxidative Annulation of Unsaturated Molecules via Directed C—H Activation[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1286-1306.

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图/表 20

图式1. 氧化剂在导向C—H键活化与不饱和分子氧化环化中的两种作用

Scheme 1. Two roles of oxidants in directed C—H bond activation and oxidative cyclization of unsaturated molecules

图式2. 可能的苯胺与炔烃的电氧化环化机理

Scheme 2. Possible mechanism of electrooxidative annulation of anilines with alkynes

图式3. 羧酸/酰胺与炔烃的电氧化环化反应

Scheme 3. Electrooxidative annulation of carboxylic acids/ amides with alkynes

图式4. 可能的羧酸和酰胺导向的电氧化环化反应催化循环

Scheme 4. Possible catalytic cycle of electrooxidative annulation directed by carboxylic acid and amide

图式5. 萘氨基甲酸酯和1-萘酚与内炔的电氧化环化反应

Scheme 5. Electrooxidative annulation of naphthalene carbamate and 1-naphthol with internal alkynes

图式6. 可能的芳基甲醇与炔烃电氧化环化反应机理

Scheme 6. Possible mechanism of electrooxidative annulation of aryl methanol with alkynes

图式7. 可能的咪唑烯烃与炔烃电氧化环化反应催化循环

Scheme 7. Proposed catalytic cycle of electrochemical dehydrocyclization of imidazolyl alkenes and alkynes

图式8. 可能的芳基亚氨酸酯与炔烃的电氧化环化反应催化循环

Scheme 8. Proposed catalytic cycle of electrooxidative annulation of imidates with alkynes in flow

图式9. 可能的铑催化电氧化[5+2]环加成催化循环

Scheme 9. Proposed catalytic cycle of rhodium-catalyzed electrooxidative [5+2] annulation

图式10. 铑催化丙烯酰胺与炔烃的电氧化环化反应

Scheme 10. Electrooxidative rhodium-catalyzed annulation of acrylamides with alkynes

图式11. 可能的铱催化丙烯酸与炔烃的电氧化环化催化机理

Scheme 11. Possible mechanism of electrooxidative iridium- catalyzed annulation of acrylic acids with alkynes

图式12. 可能的钴催化苯甲酰胺与端炔的电氧化环化反应机理

Scheme 12. Possible mechanism of electrooxidative cobalt-catalyzed annulation of benzamides with terminal alkynes

图式13. 可能的钴催化磺酰胺与炔烃的[4+2]电氧化环化催化循环

Scheme 13. Proposed catalytic cycle of electrooxidative cobalt-catalyzed [4+2] annulation of sulfonamides with alkynes

图式14. 可能的铜催化的苯甲酰胺与炔烃的串联炔基化-环化反应催化循环

Scheme 14. Possible mechanism of cupraelectro-catalyzed domino alkynylation-cyclization

图式15. 钴催化的芳基/烯基酰胺与乙烯或乙炔电氧化[4+2]环化反应

Scheme 15. Electrooxidative cobalt-catalyzed [4+2] annulation of aryl/vinyl amides with ethylene or ethyne

图式16. 可能的钴催化的酰胺与乙烯电氧化环化反应催化循环

Scheme 16. Electrooxidative cobalt-catalyzed annulation of aryl amides with ethylene

图式17. 可能的钴催化的苯甲酰胺与丙二烯的[4+2]电氧化环化反应机理

Scheme 17. Possible mechanism of Electrooxidative cobalt-catalyzed [4+2] annulation of benzamides with allenes

图式18. 可能的铑/铱催化C—H键活化电氧化烯基化-环化机理

Scheme 18. Possible mechanism of rhodium/iridium-catalyzed electrooxidative C—H alkenylation-cyclization

图式19. 钴催化C—H活化与异氰和CO的电氧化环化反应

Scheme 19. Cobaltaelectro-catalyzed C—H activation with carbon monoxide or isocyanides

图式20. 钴催化C—H活化与异氰和CO的电氧化环化反应的可能机理

Scheme 20. Possible mechanism of cobaltaelectro-catalyzed C—H activation with carbon monoxide or isocyanides

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