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1
Ruthenium catalyzed C-C bond formation via transfer hydrogenation: branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes.钌催化通过转移氢化形成碳-碳键：丙二烯与多聚甲醛及高级醛的支链选择性还原偶联反应。
Org Lett. 2008 Jul 3;10(13):2705-8. doi: 10.1021/ol800836v. Epub 2008 Jun 6.
2
Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of beta,gamma-unsaturated ketones.通过钌催化的形成碳-碳键的转移氢化反应，从醇或醛氧化水平进行二烯氢酰化反应：β,γ-不饱和酮的合成。
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3
Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination.钌催化氟化醇与丙二烯的碳-碳偶联：在β-氢消除的能量极限下的脱氢反应。
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4
anti-Aminoallylation of aldehydes via ruthenium-catalyzed transfer hydrogenative coupling of sulfonamido allenes: 1,2-aminoalcohols.通过钌催化的磺酰胺基丙二烯转移氢化偶联实现醛的抗氨甲酰化反应：1,2-氨基醇
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Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.通过钌催化转移氢化实现炔醛的还原 C-C 偶联：在不存在预金属化试剂的情况下，通过直接区域和立体选择性羰基乙烯化形成三取代烯丙醇。
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本文引用的文献

1
Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: a ruthenium-catalyzed C-C bond-forming transfer hydrogenation.使用1,3-烯炔作为预制联烯基金属试剂的替代物，从醇或醛氧化水平进行羰基炔丙基化反应：一种钌催化的碳-碳键形成转移氢化反应。
Angew Chem Int Ed Engl. 2008;47(28):5220-3. doi: 10.1002/anie.200801359.
2
Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.钌催化的碳-碳键形成转移氢化反应：以无环1,3-二烯作为预制烯丙基金属试剂的替代物，从醇或醛氧化态进行羰基烯丙基化反应。
J Am Chem Soc. 2008 May 21;130(20):6338-9. doi: 10.1021/ja801213x. Epub 2008 Apr 29.
3
Diastereo- and enantioselective hydrogenative aldol coupling of vinyl ketones: design of effective monodentate TADDOL-like phosphonite ligands.乙烯基酮的非对映和对映选择性氢化羟醛偶联反应：高效单齿类TADDOL亚磷酸酯配体的设计
J Am Chem Soc. 2008 Mar 5;130(9):2746-7. doi: 10.1021/ja710862u. Epub 2008 Feb 12.
4
Iridium-catalyzed C-C coupling via transfer hydrogenation: carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene.铱催化通过转移氢化进行的碳-碳偶联：利用1,3-环己二烯从醇或醛氧化水平进行羰基加成
Org Lett. 2008 Mar 6;10(5):1033-5. doi: 10.1021/ol800159w. Epub 2008 Feb 7.
5
Catalytic C-C coupling via transfer hydrogenation: reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level.通过转移氢化实现催化碳-碳偶联：从醇或醛氧化水平进行反向异戊烯基化、巴豆酰化和烯丙基化。
J Am Chem Soc. 2007 Dec 12;129(49):15134-5. doi: 10.1021/ja077389b. Epub 2007 Nov 17.
6
Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts.双功能过渡金属基分子催化剂用于酮的不对称转移氢化反应。
Acc Chem Res. 2007 Dec;40(12):1300-8. doi: 10.1021/ar700134q. Epub 2007 Oct 26.
7
Enantioselective iridium-catalyzed imine vinylation: optically enriched allylic amines via alkyne-imine reductive coupling mediated by hydrogen.对映选择性铱催化的亚胺乙烯基化反应：通过氢气介导的炔烃-亚胺还原偶联反应制备光学富集的烯丙基胺。
J Am Chem Soc. 2007 Oct 24;129(42):12644-5. doi: 10.1021/ja075438e. Epub 2007 Oct 3.
8
Carbonyl allylation in the absence of preformed allyl metal reagents: reverse prenylation via iridium-catalyzed hydrogenative coupling of dimethylallene.在不存在预先形成的烯丙基金属试剂的情况下进行羰基烯丙基化反应：通过铱催化的二甲基丙二烯氢化偶联实现逆异戊烯基化反应。
J Am Chem Soc. 2007 Oct 24;129(42):12678-9. doi: 10.1021/ja075971u. Epub 2007 Sep 27.
9
Enantiomerically enriched allylic alcohols and allylic amines via C-C bond-forming hydrogenation: asymmetric carbonyl and imine vinylation.通过形成碳 - 碳键的氢化反应制备对映体富集的烯丙醇和烯丙胺：不对称羰基和亚胺乙烯基化反应
Acc Chem Res. 2007 Dec;40(12):1394-401. doi: 10.1021/ar7001123. Epub 2007 Sep 5.
10
Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen.铑催化的乙烯基酮与N-磺酰亚胺的还原曼尼希偶联反应，由氢气介导。
J Org Chem. 2007 Jul 20;72(15):5843-6. doi: 10.1021/jo070779w. Epub 2007 Jun 21.

钌催化通过转移氢化形成碳-碳键：丙二烯与多聚甲醛及高级醛的支链选择性还原偶联反应。

Ruthenium catalyzed C-C bond formation via transfer hydrogenation: branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes.

作者信息

Ngai Ming-Yu, Skucas Eduardas, Krische Michael J

机构信息

University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.

出版信息

Org Lett. 2008 Jul 3;10(13):2705-8. doi: 10.1021/ol800836v. Epub 2008 Jun 6.

DOI:10.1021/ol800836v
PMID:18533665
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2845390/
Abstract

Under the conditions of ruthenium-catalyzed transfer hydrogenation employing 2-propanol as the terminal reductant, 1,1-disubstituted allenes 1a- h engage in reductive coupling to paraformaldehyde to furnish homoallylic alcohols 2a- h. Under identical transfer hydrogenation conditions, 1,1-disubstituted allenes engage in reductive coupling to aldehydes 3a- f to furnish homoallylic alcohols 4a- n. In all cases, reductive coupling occurs with branched regioselectivity to deliver homoallylic alcohols bearing all-carbon quaternary centers.

摘要

在以2-丙醇作为末端还原剂的钌催化转移氢化条件下，1,1-二取代丙二烯1a - h与多聚甲醛进行还原偶联反应，生成高烯丙醇2a - h。在相同的转移氢化条件下，1,1-二取代丙二烯与醛3a - f进行还原偶联反应，生成高烯丙醇4a - n。在所有情况下，还原偶联反应均以支链区域选择性进行，生成带有全碳季碳中心的高烯丙醇。