Derivatization of an Alkylideneborane with B=C Bond Cleavage

Han, Jixing1; Hu, Chaopeng2,4; Li, Qianli3; Liu, Liu Leo2,4; Tung, Chen-Ho1; Cui, Ping1; Kong, Lingbing1

2023-11-07

10.1021/acs.inorgchem.3c03232

INORGANIC CHEMISTRY   影响因子和分区

0020-1669

1520-510X

We present the synthesis, structural characterization, and reactivity of alkylideneborane 2, supported by p-donating N-heterocyclic imino and sigma-donating N-heterocyclic carbene (NHC) ligands. The incorporation of these ligands effectively weakens the B=C bond strength, leading to enhanced reactivity. Consequently, selective cleavage of the B=C bond can be achieved using pyridine-N-oxide, sulfur, and selenium, resulting in the formation of 1,3-dioxa-2,4-diboretane 3, thioxoborane 4, and selenoborane 5, respectively. Furthermore, intriguing B=C bond insertions with CO2 and CS2 are observed, affording zwitterionic borenium/fluorenide 6 and dithiaboretane 7. The former species 6 is readily converted to transient oxoborane and imidazolium enolate, showcasing the bora-Wittig reaction of alkylideneborane. This investigation highlights the potential of alkylideneborane as a versatile building block for synthesizing novel organoboron compounds through unconventional transformations.

SCI ; EI

英语

NI论文

通讯

Shandong University["22271174","21971144","22101114","22271132"] ; Top-Notch Young Talents Program of China[tsqn202211007] ; Taishan Scholar Project of Shandong Province of China[ZR2019ZD46] ; Natural Science Foundation of Shandong Province[2020QNQT007]

Chemistry

Chemistry, Inorganic & Nuclear

WOS:001107620500001

AMER CHEMICAL SOC

20234915145293

Chelation ; Organic compounds ; Selenium compounds ; Synthesis (chemical)

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

Web of Science

1.Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
3.Liaocheng Univ, Sch Chem & Chem Engn, Liaocheng 252059, Peoples R China
4.Southern Univ Sci & Technol, Res Ctr Chem Biol & Om Anal, Coll Sci, Shenzhen 518055, Peoples R China

Han, Jixing,Hu, Chaopeng,Li, Qianli,et al. Derivatization of an Alkylideneborane with B=C Bond Cleavage[J]. INORGANIC CHEMISTRY,2023,62(46):18820-18824.

Han, Jixing.,Hu, Chaopeng.,Li, Qianli.,Liu, Liu Leo.,Tung, Chen-Ho.,...&Kong, Lingbing.(2023).Derivatization of an Alkylideneborane with B=C Bond Cleavage.INORGANIC CHEMISTRY,62(46),18820-18824.

Han, Jixing,et al."Derivatization of an Alkylideneborane with B=C Bond Cleavage".INORGANIC CHEMISTRY 62.46(2023):18820-18824.