Transition-Metal-Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride

Ieki Ryosuke; Kani Yuria; Tsunoi Shinji; Shibata Ikuya

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Transition-Metal-Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride

机译：氢化锡锡催化乙烯基环丙烷与醛的无过渡金属偶联反应

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Donor-acceptor cyclopropanes are useful building blocks for catalytic cycloaddition reactions with a range of electrophiles to give various cyclic products. In contrast, relatively few methods are available for the synthesis of homoallylic alcohols through coupling of vinylcyclopropanes (VCPs) with aldehydes, even with transition-metal catalysts. Here, we report that the hydrostannation of vinylcyclopropanes (VCPs) was effectively promoted by dibutyliodotin hydride (Bu2SnIH). The resultant allylic tin compounds reacted easily with aldehydes. Furthermore, the use of Bu2SnIH was effectively catalytic in the presence of hydrosilane as a hydride source, which established a coupling reaction of VCPs with aldehydes for the synthesis of homoallylic alcohols without the use of transition-metal catalysts. In contrast to conventional catalytic reactions of VCPs, the presented method allowed the use of several VCPs in addition to conventional donor-acceptor cyclopropanes.

机译：供体-受体环丙烷是用于与一系列亲电试剂催化环加成反应以生成各种环状产物的有用构建基。相比之下，通过乙烯基环丙烷（VCP）与醛偶合，甚至使用过渡金属催化剂，合成均烯丙基醇的方法相对较少。在这里，我们报道乙烯基二氢丙烷（Bu2SnIH）有效地促进了乙烯基环丙烷（VCPs）的氢化。所得的烯丙基锡化合物容易与醛反应。此外，在氢硅烷作为氢化物源的情况下，Bu2SnIH的使用可有效催化，这无需合成金属催化剂即可建立VCP与醛的偶联反应，以合成均烯丙基醇。与VCP的常规催化反应相反，除了常规的供体-受体环丙烷外，本方法还允许使用多种VCP。

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《Chemistry: A European journal》 |2015年第16期|共6页
作者
Ieki Ryosuke; Kani Yuria; Tsunoi Shinji; Shibata Ikuya;
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正文语种 eng
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allylation; hydrides; hydrostannation; small-ring systems; tin;

机译：烯丙基化;氢化物;氢化锡;小环体系;锡;

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1. Transition-Metal-Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride [J] . Ieki Ryosuke, Kani Yuria, Tsunoi Shinji, Chemistry: A European journal . 2015,第16期

机译：氢化锡锡催化乙烯基环丙烷与醛的无过渡金属偶联反应
2. Ni/Pd-catalyzed Suzuki–Miyaura cross-coupling of alcohols and aldehydes and C–N cross-coupling of nitro and amines via domino redox reactions: base-free, hydride acceptor-free [J] . Milad Kazemnejadi, Rebin Omer Ahmed, Boshra Mahmoudi RSC Advances . 2020,第72期

机译：NI / PD催化的铃木宫牛醇和硝基和醛的C-N交叉偶联通过多米诺氧化物和胺的C-N交叉偶联反应：无基质，无氢化物体无
3. Synthesis of 2-Hydroxymethyl Ketones by Ruthenium Hydride-Catalyzed Cross-Coupling Reaction of r,-Unsaturated Aldehydes with Primary Alcohols [J] . Aurelien Denichoux, Takahide Fukuyama, Takashi Doi, Organic letters . 2010,第1期

机译：氢化钌催化r，-不饱和醛与伯醇的交叉偶联反应合成2-羟基甲基酮
4. Ni-Catalyzed Multi-component Coupling Reaction of Organozinc, 1,3-Dienes Aldehydes, and Amines Promoted by Alkynes as a Spectator Ligand [C] . Yasushi Tatsuyama, Takahiro Yamada, Shinji Ozaki Symposium on Organometallic Chemistry . 2007

机译：Ni催化有机锌，1,3-二烯醛的多组分偶联反应，并作为alkynes作为观众配体促进的胺
5. I. Heterogeneous cross-coupling reactions catalyzed by nickel-in-charcoal and copper-in-charcoal. II. Asymmetric 1,2/1,4-reductions catalyzed by copper hydride. III. Atropselective synthesis of the biaryl A-B ring system of vancomycin utilizing an internally tethered, nonracemic ligand. [D] . Lee, Ching-Tien. 2009

机译：I.炭中镍和炭中铜催化的非均相交叉偶联反应。二。氢化铜催化的不对称1,2 / 1,4-还原反应。三，利用内部束缚的非外消旋配体进行万古霉素联芳基A-B环系统的选择性催化合成。
6. C–H Bond Functionalization via Hydride Transfer: Lewis Acid Catalyzed Alkylation Reactions by Direct Intramolecular Coupling of sp3 C–H Bonds and Reactive Alkenyl Oxocarbenium Intermediates [O] . Kevin M. McQuaid, Dalibor Sames -1

机译：通过氢化物转移的C–H键功能化：路易斯酸通过sp3 C–H键与反应性烯基氧碳Inter中间体的直接分子内偶联反应催化烷基化反应
7. Electrogenerated Acid-Catalyzed Reactions of Acetals, Aldehydes, and Ketones with Organosilicon Compounds, Leading to Aldol Reactions, Allylations, Cyanations, and Hydride Additions [O] . Sigeru Torii, Tsutomu Inokuchi, Sadahito Takagishi, 1987

机译：用有机硅化合物的丙酮，醛和酮的电流酸催化反应，导致醛醇反应，烯丙基，氰和氢化物添加剂
8. Transition-Metal-Promoted Reactions of Boron Hydrides. 7. Platinum(II) Bromide Catalyzed Cage Growth and Dehydrocoupling Reactions of Diborane with Small Polyhedral Carboranes and Boranes: Synthesis of a New Arachno Carborane, 5,6-C2B6H12, and the Diborane-Coupled Compounds 2:1', 2'-(1,6-C2B4H5)(B2H5) and 2:1',2'-(B5H8)(B2H5). [R] . Corcoran, E. W., Sneddon, L. G. 1985

机译：过渡金属促进的氢化硼反应。 7.铂（II）溴化物催化的笼型生长和乙硼烷与小多面体碳硼烷和硼烷的脱氢偶联反应：合成新的arachno Carborane，5,6-C2B6H12和乙硼烷偶联化合物2：1'，2' - （ 1,6-C2B4H5）（B2H5）和2：1'，2' - （B5H8）（B2H5）。

Transition-Metal-Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride

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