Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes

Semba K.; Shinomiya M.; Fujihara T.; Terao J.; Tsuji Y.

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Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes

机译：铜的高选择性催化烯和1,3-二烯的硼氢化

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The highly selective copper-catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a (Z)-σ-allyl copper species, which was isolated and structurally characterized by single-crystal X-ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3-diene derivatives to afford allylboranes and homoallylboranes.

机译：已经开发出高度选择性的铜催化的艾伦硼氢化。通过明智地选择催化物种（氢化铜和硼基铜），选择性地制备烯丙基硼烷和烯基硼烷。此外，通过选择合适的配体可以选择性地合成两种类型的烯基硼烷。机理研究证实，通过单晶X射线衍射分离并在结构上表征的（Z）-σ-烯丙基铜物质的质子化是这些反应的关键步骤。除丙二烯外，该方法还可用于1，3-二烯衍生物的选择性加氢硼化，以制得烯丙基硼烷和均烯丙二烯。

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《Chemistry: A European journal》 |2013年第22期|共8页
作者
Semba K.; Shinomiya M.; Fujihara T.; Terao J.; Tsuji Y.;
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正文语种 eng
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allenes; copper; dienes; hydroboration; ligand effects;

机译：丙二烯;铜;二烯;硼氢化;配体效应;

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1. Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes [J] . Semba K., Shinomiya M., Fujihara T., Chemistry: A European journal . 2013,第22期

机译：铜的高选择性催化烯和1,3-二烯的硼氢化
2. Rhodium-catalyzed highly diastereoselective intramolecular [4+2] cycloaddition of 1,3-disubstituted allene-1,3-dienes [J] . Han Yulin, Ma Shengming Organic Chemistry Frontiers . 2018,第18期

机译：铑催化的高度非映选择性分子内[4 + 2]环加成1,3-二取代的联烯-1,3-二烯
3. Silaborations of 1,3-enynes - Substrate controlled allene/1,3-diene selectively [J] . Luken C, Moberg C Organic letters . 2008,第12期

机译：1,3-烯炔的硅烷化-底物选择性控制的Allene / 1,3-二烯
4. Highly Selective Addition of Arylboronic Acids to 1,3-Dienes Catalyzed by an Iridium Complex [C] . Takahiro Nishimura, Yuichi Yasuhara, Tamio Hayashi Symposium on Organometallic Chemistry . 2007

机译：通过铱络合物催化的1,3-二烯的高度选择性加入芳基硼酸至1,3-二烯
5. Discovery and development of 3,3,3-trichloropropyl-1-triphenylphosphonium chloride: A reagent for synthesis of Z-1,3-enynes, Z,Z-1-chloro-1,3-dienes and 1,3-diynes [D] . Karatholuvhu, Maheswaran S. 2006

机译：3,3,3-三氯丙基-1-三苯基氯化chloride的发现与开发：用于合成Z-1,3-烯，Z，Z-1-氯-1,3-二烯和1,3-二炔的试剂
6. Enantioselective Synthesis of (E)-δ-Stannyl Homoallylic Alcohols Via Aldehyde Allylboration Using α-Stannylallylboranes Generated by Allene Hydroboration Followed By a Highly Diastereoselective 13-Boratropic Shift [O] . Ming Chen, Daniel H. Ess, William R. Roush -1

机译：的对映体选择性合成（E）-δ-甲锡烷基高烯丙醇通过醛allylboration使用α-stannylallylboranes由丙二烯硼氢化生成随后是高度非对映13- Boratropic移
7. Enantioselective Synthesis of (E)-δ-Stannyl Homoallylic Alcohols via Aldehyde Allylboration Using α-Stannylallylboranes Generated by Allene Hydroboration Followed by a Highly Diastereoselective 1,3-Boratropic Shift [O] . Ming Chen, Daniel H. Ess, William R. Roush 2010

机译：通过α-甾烷基烯丙基硼酸烷基通过由烯烯氢化物产生的α-甾烷基烯丙基硼酸烷基酰化合成（e）-δ-甾烷基官醇醇的致注重合成α-甾烷基烯丙基硼酸烷基，其次是高度非分析的1,3-硼散

Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes

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