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环酮肟酯的无过渡金属C-C键裂解/硼化反应

Transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters.

作者信息

Zhang Jin-Jiang, Duan Xin-Hua, Wu Yong, Yang Jun-Cheng, Guo Li-Na

机构信息

Department of Chemistry , School of Science , MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter , Xi'an Jiaotong University , Xi'an , Shaanxi 710049 , China . Email:

出版信息

Chem Sci. 2018 Oct 2;10(1):161-166. doi: 10.1039/c8sc03315c. eCollection 2019 Jan 7.

DOI:10.1039/c8sc03315c
PMID:30713627
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6328001/
Abstract

An efficient transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B(OH) reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base. This complex could be used as an efficient single electron reductant in other ring-opening transformations of cycloketone oxime esters. Free-radical trapping, radical-clock, and DFT calculations all suggest a radical pathway for this transformation.

摘要

已报道了一种高效的无过渡金属催化的环酮肟酯的碳-碳键裂解/硼化反应。在该反应中，B(OH)试剂不仅作为硼源，还通过与类似DMAc的路易斯碱形成配合物充当电子供体源。这种配合物可在环酮肟酯的其他开环转化反应中用作有效的单电子还原剂。自由基捕获、自由基钟实验和密度泛函理论计算均表明该转化反应是通过自由基途径进行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/77a6025dd20f/c8sc03315c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/cc72ad2120c2/c8sc03315c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/8a3128f002d0/c8sc03315c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/57bba6c84fe3/c8sc03315c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/18d7fda9b5c8/c8sc03315c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/fe3402b8948a/c8sc03315c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/77a6025dd20f/c8sc03315c-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/cc72ad2120c2/c8sc03315c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/8a3128f002d0/c8sc03315c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/57bba6c84fe3/c8sc03315c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/18d7fda9b5c8/c8sc03315c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/fe3402b8948a/c8sc03315c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3ae/6328001/77a6025dd20f/c8sc03315c-f4.jpg

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