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真正的卡宾难题。

The Genuine Carbene Conundrum.

作者信息

Sawyer Bethany, Peltier Jesse L, Jazzar Rodolphe

机构信息

Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA, 92182, USA.

Departments of Chemistry & Chemical Biology, and Chemical Engineering, Northeastern University, 360 Huntington Ave, Boston, MA, 02115, USA.

出版信息

Chemistry. 2025 Aug 7;31(44):e202501600. doi: 10.1002/chem.202501600. Epub 2025 Jun 25.

DOI:10.1002/chem.202501600
PMID:40460197
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12336776/
Abstract

Carbenes, these neutral divalent carbon species have emerged as pivotal players in our laboratories. Despite their broad impact, direct characterization of these reactive molecules remains challenging in many cases. This concept article draws on recent literature to explore the strengths and limitations of the most widely used strategies for their identification.

摘要

卡宾，这些中性二价碳物种已在我们的实验室中成为关键角色。尽管它们具有广泛影响，但在许多情况下，对这些活性分子进行直接表征仍然具有挑战性。这篇概念文章借鉴近期文献，探讨了用于识别它们的最广泛使用策略的优势和局限性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/0ce7f5af8a3c/CHEM-31-e202501600-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/3e97dad87651/CHEM-31-e202501600-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/0cd7d54bccca/CHEM-31-e202501600-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/a79194778ca1/CHEM-31-e202501600-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/a73957880088/CHEM-31-e202501600-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/ee449cb80559/CHEM-31-e202501600-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/c49c4efbd43a/CHEM-31-e202501600-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/20ab762ee42a/CHEM-31-e202501600-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/ca0f550e2730/CHEM-31-e202501600-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/e813f20aab6f/CHEM-31-e202501600-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/0ce7f5af8a3c/CHEM-31-e202501600-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/3e97dad87651/CHEM-31-e202501600-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/0cd7d54bccca/CHEM-31-e202501600-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/a79194778ca1/CHEM-31-e202501600-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/a73957880088/CHEM-31-e202501600-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/ee449cb80559/CHEM-31-e202501600-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/c49c4efbd43a/CHEM-31-e202501600-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/20ab762ee42a/CHEM-31-e202501600-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/ca0f550e2730/CHEM-31-e202501600-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/e813f20aab6f/CHEM-31-e202501600-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c65a/12336776/0ce7f5af8a3c/CHEM-31-e202501600-g004.jpg

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本文引用的文献

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A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene.一种晶态稠合吡啶-1-亚基及其异构化为吡啶-3-亚基的过程。
J Am Chem Soc. 2025 May 7;147(18):14972-14977. doi: 10.1021/jacs.5c05642. Epub 2025 Apr 28.
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Singlet Carbenes Are Stereoinductive Main Group Ambiphiles.单线态卡宾是具有立体诱导性的主族双亲体。
J Am Chem Soc. 2025 Apr 30;147(17):14777-14784. doi: 10.1021/jacs.5c03845. Epub 2025 Apr 21.
3
Cyclic (Alkenyl)(Amino)Carbene (CAAC): Introducing a Member to the Cyclic (Alkyl)(Amino)Carbenes Family Featuring a Narrow Energy Gap.
环状（烯基）（氨基）卡宾（CAAC）：向具有窄能隙的环状（烷基）（氨基）卡宾家族引入一名成员。
J Am Chem Soc. 2025 Feb 26;147(8):6905-6913. doi: 10.1021/jacs.4c17319. Epub 2025 Feb 17.
4
Wolff Rearrangement of a Metalated Diazoester: Structural Confirmation of the Singlet Carbene Wolff-Intermediate.金属化重氮酯的沃尔夫重排：单线态卡宾沃尔夫中间体的结构确证
J Am Chem Soc. 2025 Feb 19;147(7):5590-5595. doi: 10.1021/jacs.4c18289. Epub 2025 Feb 11.
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Radical Brook rearrangement: past, present, and future.自由基布鲁克重排反应：过去、现在与未来。
Chem Soc Rev. 2025 Feb 17;54(4):1870-1904. doi: 10.1039/d4cs01275e.
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The influential IPr: 25 years after its discovery.有影响力的IPr：发现25年后
Chem Sci. 2025 Jan 9;16(5):2062-2082. doi: 10.1039/d4sc07009g. eCollection 2025 Jan 29.
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N-Heterocyclic carbene (NHC) organocatalysis: from fundamentals to frontiers.N-杂环卡宾（NHC）有机催化：从基础到前沿
Chem Soc Rev. 2025 Feb 3;54(3):1102-1124. doi: 10.1039/d4cs01179a.
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A Strongly Ambiphilic Ferrocene-Based Cyclic (Alkyl)(amino)carbene - Specific Decomposition to an Enamine by a 1,2-Phenyl Shift.一种基于二茂铁的强两亲性环状（烷基）（氨基）卡宾——通过1,2-苯基迁移特异性分解为烯胺。
Chemistry. 2024 Dec 10;30(69):e202403028. doi: 10.1002/chem.202403028. Epub 2024 Oct 29.
9
Genuine carbene versus carbene-like reactivity.真正的卡宾与类卡宾反应活性
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