| Title: | Difluoroacetaldehyde N-Triftosylhydrazone (DFHZ-Tfs) as a Bench-Stable Crystalline Diazo Surrogate for Diazoacetaldehyde and Difluorodiazoethane |
| Author(s): | Ning Y; Zhang X; Gai Y; Dong Y; Sivaguru P; Wang Y; Reddy BRP; Zanoni G; Bi X; |
| Address: | "Department of Chemistry, Northeast Normal University, Changchun, 130024, China. Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China" |
| ISSN/ISBN: | 1521-3773 (Electronic) 1433-7851 (Linking) |
| Abstract: | "Despite the growing importance of volatile functionalized diazoalkanes in organic synthesis, their safe generation and utilization remain a formidable challenge because of their difficult handling along with storage and security issues. In this study, we developed a bench-stable difluoroacetaldehyde N-triftosylhydrazone (DFHZ-Tfs) as an operationally safe diazo surrogate that can release in situ two low-molecular-weight diazoalkanes, diazoacetaldehyde (CHOCHN(2) ) or difluorodiazoethane (CF(2) HCHN(2) ), in a controlled fashion under specific conditions. DFHZ-Tfs has been successfully employed in the Fe-catalyzed cyclopropanation and Doyle-Kirmse reactions, thus highlighting the synthetic utility of DFHZ-Tfs in the efficient construction of molecule frameworks containing CHO or CF(2) H groups. Moreover, the reaction mechanism for the generation of CHOCHN(2) from CF(2) HCHN(2) was elucidated by density functional theory (DFT) calculations" |
| Keywords: | Doyle-Kirmse reaction cyclopropanation density functional calculations diazo compounds difluoroacetaldehyde N-triftosylhydrazone; |
| Notes: | "PubMed-not-MEDLINENing, Yongquan Zhang, Xinyu Gai, Yi Dong, Yuanqing Sivaguru, Paramasivam Wang, Yingying Reddy, Bhoomireddy Rajendra Prasad Zanoni, Giuseppe Bi, Xihe eng Research Support, Non-U.S. Gov't Germany 2020/01/31 Angew Chem Int Ed Engl. 2020 Apr 16; 59(16):6473-6481. doi: 10.1002/anie.202000119. Epub 2020 Mar 2" |
