Synthesis and applications of α-trifluoromethylated alkylboron compounds.
Synthesis and applications of α-trifluoromethylated alkylboron compounds.
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DOI：
10.1002/anie.201308036
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发表时间：
2013-12-16
影响因子：
16.6
通讯作者：
Molander, Gary A.
中科院分区：
文献类型：
--
作者：
Argintaru, O. Andreea;Ryu, DaWeon;Aron, Ioana;Molander, Gary A.
在制药、农用化学品和材料工业中，将氟化亚基纳入有机分子的重要性是公认的。1,2因此，开发以安全、选择性和简便的方式将这些氟化部分纳入有机基质的方法一直是一个非常有趣的领域。在各种氟化基团中，强吸电子的三氟甲基（CF3）因其植入分子后能产生的深刻特性而受到广泛关注。然而，大多数合成努力都集中在功能化芳烃中引入CF3。相比之下，将CF3并入烷基体系的一般方法还不太发达，但在结构多样性和扩大化学空间方面变得越来越重要。9 β-三氟乙基碳离子合成子代表了一套有吸引力的试剂，用于在烷基构建块领域内安装氟化亚结构。然而，由于金属-氟（M-F）键形成的强大驱动力，M-F部分的β-消除倾向很高（eq 1），因此β三氟乙基碳离子合成子的化学研究非常有限和不发达。10
The importance of incorporating fluorinated subunits into organic molecules is well established in the pharmaceutical, agrochemical, and materials industries. 1, 2 Developing methods of incorporating such fluorinated moieties into organic substrates in a safe, selective, and facile manner, therefore, has been an area of great interest. 3 Among the various fluorinated moieties, the strongly electron-withdrawing trifluoromethyl group (CF3) has garnered much attention because of the profound properties it can effect upon being implanted within a molecule. 4 However, most of the synthetic efforts have been focused on introducing CF3 in functionalized arenes. 5By contrast, general methods for the incorporation of CF3 into alkyl systems is less well developed, 6–8 yet increasingly more important in terms of structural diversity and expanding chemical space. 9 β-Trifluoroethyl carbanion synthons represent an attractive set of reagents for the installation of fluorinated substructures within the realm of alkyl building blocks. However, owing to a strong driving force for the formation of metal-fluorine (M–F) bonds, the propensity for β-elimination of M–F moieties is high (eq 1), and thus the chemistry of βtrifluoroethyl carbanion synthons is astonishingly limited and underdeveloped. 10
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影响因子：
15
作者：
Knapp DM;Gillis EP;Burke MD
通讯作者：
Burke MD
影响因子：
5.2
作者：
Chu, Lingling;Qing, Feng-Ling
通讯作者：
Qing, Feng-Ling
影响因子：
15
作者：
Deng, Qing-Hai;Wadepohl, Hubert;Gade, Lutz H.
通讯作者：
Gade, Lutz H.
影响因子：
15
作者：
Herrmann, Aaron T.;Smith, Lindsay L.;Zakarian, Armen
通讯作者：
Zakarian, Armen
钯催化末端炔烃与 1,1,1-三氟-2-碘乙烷的三氟乙基化
影响因子：
5.2
作者：
Feng, Yi-Si;Xie, Chuan-Qi;Xu, Hua-Jian
通讯作者：
Xu, Hua-Jian