Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp)-H and C(sp)-H bonds

Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nev...

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Published inOrganic & biomolecular chemistry Vol. 22; no. 4; pp. 645 - 681
Main Authors Wang, Chang-Sheng, Xu, Yuan, Wang, Shao-Peng, Zheng, Chun-Ling, Wang, Guowei, Sun, Qiao
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 24.01.2024
Subjects
Agrochemicals
Aromatic compounds
Chelation
Chemical bonds
Electrochemistry
Intermediates
Natural products
Polymers
Substrates
Transition metals
Online AccessGet full text
ISSN1477-0520
1477-0539
1477-0539
DOI10.1039/d3ob01847d

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Abstract Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C-H chalcogenation severely lags behind C-C, C-N and C-O bond formations. Moreover, compared with the C-H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C-H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp 2 )-H and C(sp 3 )-H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C-H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C-H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C-H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp 3 )-H dichalcogenation; (4) dichalcogenation of both C(sp 2 )-H and C(sp 3 )-H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery. This review comprehensively summarizes the recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of various C-H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches.
AbstractList Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C-H chalcogenation severely lags behind C-C, C-N and C-O bond formations. Moreover, compared with the C-H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C-H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp 2 )-H and C(sp 3 )-H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C-H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C-H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C-H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp 3 )-H dichalcogenation; (4) dichalcogenation of both C(sp 2 )-H and C(sp 3 )-H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery. This review comprehensively summarizes the recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of various C-H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches.
Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C–H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C–H chalcogenation severely lags behind C–C, C–N and C–O bond formations. Moreover, compared with the C–H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C–H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp2)–H and C(sp3)–H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C–H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C–H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C–H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp3)–H dichalcogenation; (4) dichalcogenation of both C(sp2)–H and C(sp3)–H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery.
Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C-H chalcogenation severely lags behind C-C, C-N and C-O bond formations. Moreover, compared with the C-H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C-H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp2)-H and C(sp3)-H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C-H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C-H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C-H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp3)-H dichalcogenation; (4) dichalcogenation of both C(sp2)-H and C(sp3)-H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery.Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C-H chalcogenation severely lags behind C-C, C-N and C-O bond formations. Moreover, compared with the C-H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C-H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp2)-H and C(sp3)-H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C-H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C-H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C-H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp3)-H dichalcogenation; (4) dichalcogenation of both C(sp2)-H and C(sp3)-H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery.
Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C-H chalcogenation severely lags behind C-C, C-N and C-O bond formations. Moreover, compared with the C-H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C-H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp )-H and C(sp )-H bonds transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C-H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C-H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C-H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp )-H dichalcogenation; (4) dichalcogenation of both C(sp )-H and C(sp )-H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery.
Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C–H bonds has evolved as a step- and atom-economical method for the synthesis of chalcogen-bearing compounds. Nevertheless, direct C–H chalcogenation severely lags behind C–C, C–N and C–O bond formations. Moreover, compared with the C–H monochalcogenation, reports of selective mono-/dichalcogenation and exclusive dichalcogenation of C–H bonds are relatively scarce. The past decade has witnessed significant advancements in selective mono-/dichalcogenation and exclusive dichalcogenation of various C(sp 2 )–H and C(sp 3 )–H bonds via transition-metal-catalyzed/mediated, photocatalytic, electrochemical or metal-free approaches. In light of the significance of both mono- and dichalcogen-containing compounds in various fields of chemical science and the critical issue of chemoselectivity in organic synthesis, the present review systematically summarizes the advances in these research fields, with a special focus on elucidating scopes and mechanistic aspects. Moreover, the synthetic limitations, applications of some of these processes, the current challenges and our own perspectives on these highly active research fields are also discussed. Based on the substrate types and C–H bonds being chalcogenated, the present review is organized into four sections: (1) transition-metal-catalyzed/mediated chelation-assisted selective C–H mono-/dichalcogenation or exclusive dichalcogenation of (hetero)arenes; (2) directing group-free selective C–H mono-/dichalcogenation or exclusive dichalcogenation of electron-rich (hetero)arenes; (3) C(sp 3 )–H dichalcogenation; (4) dichalcogenation of both C(sp 2 )–H and C(sp 3 )–H bonds. We believe the present review will serve as an invaluable resource for future innovations and drug discovery.
Author Xu, Yuan
Wang, Chang-Sheng
Sun, Qiao
Wang, Guowei
Wang, Shao-Peng
Zheng, Chun-Ling
AuthorAffiliation Nanjing Tech University
School of Food Science and Light Industry
School of Biotechnology and Pharmaceutical Engineering
Chemical Engineering and Biotechnology
School of Chemistry
Nanyang Technological University
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/38180073$$D View this record in MEDLINE/PubMed
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Notes Shao-Peng Wang was born in Guangxi Province (China) in 2000. In 2022, he received his Bachelor's degree from Nanjing Tech University. He has continued to pursue a Master's degree at the same university since then. His research mainly focuses on the electrochemical C-H amination reactions.
Chun-Ling Zheng was born in Hubei Province (China). She received her Master's degree in Textile Chemistry and Dyeing & Finishing Engineering from Soochow University in 2005. The same year, she began her Ph.D. studies at the lab of Professor Yukio Nagaosa at Fukui University, Japan, where she focused on the development of natural chemicals. In 2009, she began her independent career at Nanjing Tech University. Her research interest focuses on the fields of structural modification and application of natural organic compounds.
Yuan Xu completed his undergraduate and graduate studies at Soochow University in China, where he earned both a Bachelor's and Master's degree. He then pursued his Ph.D. Degree at Nanyang Technological University (NTU) in Singapore, specializing in the field of organic synthesis and antimicrobial drug development. After successfully completing his doctoral studies, he continued his research journey as a postdoctoral fellow at NTU. During this pivotal period, his work primarily focuses on carbohydrate synthesis and its practical applications in addressing challenges in the realms of medicine and biochemistry.
Guowei Wang was born in Sichuan Province (China). He obtained his Master's degree from Sichuan University in 2002. Then he began his independent career at Nanjing Tech University. Meanwhile, he began his Ph.D. studies of Applied Chemistry at the lab of Professor Jintang Wang at Nanjing Tech University, where he focused on the preparation and application of novel thiazole compounds. In recent five years, his research interest focuses on the preparation and application of ionic liquids and surface-active ionic liquids.
Qiao Sun received her Bachelor's degree from Sichuan University (2010) and Master's degree from the University of Chinese Academy of Sciences (2013) under the supervision of Prof. Sheng Jiang. In 2019, he obtained her Ph.D. degree in Organic Chemistry from NTU Singapore under the supervision of Prof. Naohiko Yoshikai. Then she spent two years in Shanghai STA Pharmaceutical as a senior researcher, working on the high-throughput screening and optimization of chemical processes. In 2023, she joined Nanjing Tech University as a research associate professor and her research interests include organic synthetic methodology, medical chemistry, and high throughput-screening.
Chang-Sheng Wang obtained his Bachelor's degree in 2012 and Master's degree (Joint Master's Program with SIOC in Prof. Qi-Long Shen's group) in 2015 from Nanjing Tech University under the supervision of Prof. Cheng Yao. In 2018, he obtained his Ph.D. degree from the University of Rennes 1 under the supervision of Prof. P. H. Dixneuf and Dr Jean-François Soulé supported by CSC Scholarship. After three years' Postdoctoral research in Prof. Naohiko Yoshikai's group at NTU Singapore, he started his independent career at Nanjing Tech University as a research professor. His research interests include organic synthetic methodology, bio-transformations and flow chemistry.
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Snippet Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic...
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SubjectTerms Agrochemicals
Aromatic compounds
Chelation
Chemical bonds
Electrochemistry
Intermediates
Natural products
Polymers
Substrates
Transition metals
Title Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp)-H and C(sp)-H bonds
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