Mohammad Sadegh Karimtabar, Yasin Mohammadkhani, Mohammad Mahdavi, Parviz Rashidi Ranjbar
{"title":"The Role of 1,2-Palladium Migration/Insertion on C(sp<sup>3</sup>)-H Functionalization.","authors":"Mohammad Sadegh Karimtabar, Yasin Mohammadkhani, Mohammad Mahdavi, Parviz Rashidi Ranjbar","doi":"10.1021/acsorginorgau.5c00085","DOIUrl":"10.1021/acsorginorgau.5c00085","url":null,"abstract":"<p><p>Selective functionalization of C-(sp<sup>3</sup>)-H bonds remains challenging yet crucial for researchers. A frequently used approach by chemists to tackle this challenge involves leveraging 1,2-metal migration/insertion, which enables the selective activation and cleavage of a specific C-(sp<sup>3</sup>)-H bond adjacent to or distant from the directing group. Palladium is among the most commonly employed catalysts for C-(sp<sup>3</sup>)-H functionalization through metal migration/insertion, with Pd-(OAc)<sub>2</sub> being the predominant palladium complex utilized in these processes. 1,2-Palladium migration is a key strategy for achieving selective C-(sp<sup>3</sup>)-H functionalization. After palladium coordinates to a directing group, its migration can activate the nearby C-(sp<sup>3</sup>)-H bond. With subsequent migrations, more distant C-(sp<sup>3</sup>)-H bonds can be targeted and transformed into C-(sp<sup>3</sup>)-functional groups. During the 1,2-insertion of palladium, the migration of palladium takes place following the activation of the C-(sp<sup>3</sup>)-H bond. This migration step typically involves the palladium inserting into a double bond, which links the C-(sp<sup>3</sup>)-H bond to a C-(sp<sup>2</sup>)-H bond, thereby progressing the reaction. Ultimately, this review highlights that C-(sp<sup>3</sup>)-H functionalization via 1,2-palladium migration/insertion has the potential to selectively modify both proximal and remote C-H bonds in organic molecules, offering a valuable tool for researchers to synthesize a wide range of organic compounds in future studies. This account encompasses all types of 1,2-palladium migration/insertion and examines their impact on C-(sp<sup>3</sup>)-H functionalization. It provides a detailed analysis of the mechanisms involved and explores how these migrations enable the activation of both remote and proximal C-(sp<sup>3</sup>)-H bonds with the directing group.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 5","pages":"299-321"},"PeriodicalIF":3.3,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12492045/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145233508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Michał Biedrzycki, Jaime Martín, Alexandre Genoux, Elia Boschi, Cristina Nevado
{"title":"Synthesis of (P^N^C)Gold(III) Complexes via Tandem Oxidative Addition/C-H Auration.","authors":"Michał Biedrzycki, Jaime Martín, Alexandre Genoux, Elia Boschi, Cristina Nevado","doi":"10.1021/acsorginorgau.5c00057","DOIUrl":"10.1021/acsorginorgau.5c00057","url":null,"abstract":"<p><p>A new method for the synthesis of cyclometalated gold-(III) complexes featuring (P^N^C) ligands is reported. This protocol employs a tandem oxidative addition/cycloauration process, enabling the formation of (P^N^C)-gold-(III)-aryl, -alkenyl and -alkynyl derivatives by creating two Au-C bonds in one pot from a structurally diverse range of C-(sp<sup>2</sup>)- and C-(sp)-iodide substrates. Additionally, a complementary two-step method was developed to access (P^N^C)-gold-(III)-alkynyl complexes, which exhibit emission in the blue and green light regions.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 5","pages":"322-327"},"PeriodicalIF":3.3,"publicationDate":"2025-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12492041/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145233481","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Mariam Abd El Sater, Floriane René, Nicolas Blanchard, Jorge Juan Cabrera-Trujillo, Karinne Miqueu* and Vincent Bizet*,
{"title":"","authors":"Mariam Abd El Sater, Floriane René, Nicolas Blanchard, Jorge Juan Cabrera-Trujillo, Karinne Miqueu* and Vincent Bizet*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 4","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":3.3,"publicationDate":"2025-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acsorginorgau.5c00042","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144779251","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Olaf Tjabben, Tatiana Besset* and Olga García Mancheño*,
{"title":"","authors":"Olaf Tjabben, Tatiana Besset* and Olga García Mancheño*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 4","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":3.3,"publicationDate":"2025-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acsorginorgau.5c00034","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144779256","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Squire J. Booker, Stephanie L. Brock, Xiangdong Li, Géraldine Masson, Sébastien Perrier, Vivek V. Ranade, Raymond E. Schaak, Gemma C. Solomon and Shelley D. Minteer*,
{"title":"","authors":"Squire J. Booker, Stephanie L. Brock, Xiangdong Li, Géraldine Masson, Sébastien Perrier, Vivek V. Ranade, Raymond E. Schaak, Gemma C. Solomon and Shelley D. Minteer*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 4","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":3.3,"publicationDate":"2025-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acsorginorgau.5c00062","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144779249","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Marcelo H. R. Carvalho, Pedro P. De Castro*, Pedro Beck, Hélio F. Dos Santos, Fabricio Machado, José R. Correa, Brenno A. D. Neto* and Giovanni W. Amarante*,
{"title":"","authors":"Marcelo H. R. Carvalho, Pedro P. De Castro*, Pedro Beck, Hélio F. Dos Santos, Fabricio Machado, José R. Correa, Brenno A. D. Neto* and Giovanni W. Amarante*, ","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 4","pages":"XXX-XXX XXX-XXX"},"PeriodicalIF":3.3,"publicationDate":"2025-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acsorginorgau.5c00049","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144779257","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}