Stereoselective Silylcupration of Conjugated Alkynes in Water at Room Temperature

Linstadt, Roscoe T. H.; Peterson, Carl A.; Lippincott, Daniel J.; Jette, Carina I.; Lipshutz, Bruce H.

doi:10.1002/anie.201311035

Cited by 60 publications

(27 citation statements)

References 28 publications

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“…10 This technology allows a desired transformation, using water-insoluble reagents, to occur without using organic solvents. Several types of reactions have been studied using nanomicelles in water: 11 Heck, Sonogashira, Stille, Negishi and Suzuki couplings, alkene metathesis, [9][10][11][12] SNAr, 13 silylcupration of alkynes, 14 and hydrophosphination. We started our investigation using propargyl acetate as the starting alkyne.…”

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confidence: 99%

Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water

et al. 2016

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confidence: 99%

Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water

et al. 2016

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“…However, stoichiometric amounts of Fleming’s silyl cuprate reagents (CuSi) by employing silyl–lithium (SiLi)8 or silyl–stannane (SiSn)9 reagents as the silicon sources are needed for this transformation. Recently, much attention has been directed toward the catalytic formation of functionalized vinylsilanes under copper catalysis, in which the key CuSi species arise from activation of disilane (SiSi)10 or silylborane (SiB) reagents11–14 (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Tb₂Al₃Ge₃, a New Partly Disordered Structure Type with Al₃ Triangles

Gladyshevskii

Lutsyshyn

Černý

et al. 2014

Zeitschrift anorg allge chemie

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Using X‐ray diffraction it was established that the actual composition of the ternary compound reported as “TbAl2Ge” is close to Tb2Al3Ge3 (refined Tb2Al3.039(1)Ge3). Differential thermal analysis showed that the compound exists in a narrow temperature range from 618 to 748 °C. The crystal structure was determined from X‐ray powder and single‐crystal diffraction data. An initial model was constructed from CaAl2Si2‐ and AlB2‐ (or LiBaSi‐) type slabs. A more detailed investigation revealed that, instead of LiBaSi‐type slabs (where the small atoms form planar nets), the structure contains ScAuSi‐type slabs (corrugated nets), where 1/6 of the Tb atoms have been removed in an ordered way, leading to a rhombohedral superlattice. The final structure represents a new structure type: Pearson symbol hR234–41.06, space group R$\bar{3}$c, a = 7.2432(3), c = 87.998(8) Å. Part of the Al atoms in the Tb‐deficient ScAuSi‐type slabs occupy a site that forms Al3 triangles. The structure of Tb2Al3Ge3 is thus closely related to the rhombohedral ErNi3Al9 and orthorhombic Y2Co3Ga9 structure types, which contain one‐atom thick Er2Al3 (Y2Ga3) layers formed by rare‐earth metal atoms and Al3 (Ga3) triangles. Compounds isotypic with Tb2Al3Ge3 were found in the systems Y‐Al‐Ge and Gd‐Al‐Ge.

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“…[1] They are not only robust synthetic equivalents of carbonyl compounds (courtesy of the Fleming-Tamao oxidation), [2] but they serve as versatile, low-cost, non-toxic coupling partners in the important Hiyama cross-coupling. [4] In comparison to the well-established [4][5][6][7][8][9] silylation of alkynes, the silylation of readily-prepared and stable allenes is currently under developed even though it offers a wider selection of regioisomeric outcomes. [4] In comparison to the well-established [4][5][6][7][8][9] silylation of alkynes, the silylation of readily-prepared and stable allenes is currently under developed even though it offers a wider selection of regioisomeric outcomes.…”

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confidence: 99%