85443-40-9Relevant academic research and scientific papers
Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis
Chiu, Hsin-Chun,Tonks, Ian A.
, p. 6090 - 6094 (2018)
Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido comple
Geometric E→Z Isomerisation of Alkenyl Silanes by Selective Energy Transfer Catalysis: Stereodivergent Synthesis of Triarylethylenes via a Formal anti-Metallometallation
Fa?bender, Svenja I.,Molloy, John J.,Mück-Lichtenfeld, Christian,Gilmour, Ryan
supporting information, p. 18619 - 18626 (2019/11/16)
An efficient geometrical E→Z isomerisation of alkenyl silanes is disclosed via selective energy transfer using an inexpensive organic sensitiser. Characterised by operational simplicity, short reaction times (2 h), and broad substrate tolerance, the reaction displays high selectivity for trisubstituted systems (Z/E up to 95:5). In contrast to thermal activation, directionality results from deconjugation of the π-system in the Z-isomer due to A1,3-strain thereby inhibiting re-activation. The structural importance of the β-substituent logically prompted an investigation of mixed bis-nucleophiles (Si, Sn, B). These versatile linchpins also undergo facile isomerisation, thereby enabling a formal anti-metallometallation. Mechanistic interrogation, supported by a theoretical investigation, is disclosed together with application of the products to the stereospecific synthesis of biologically relevant target structures.
Et2Zn-mediated stoichiometric C(sp)-H silylation of 1-alkynes and chlorosilanes
Huang, Pan,Xu, Dawen,Reich, Robert M.,Kaiser, Felix,Liu, Boping,Kühn, Fritz E.
supporting information, p. 1574 - 1577 (2019/05/17)
A first example of an Et2Zn mediated silylation of 1-aklynes is reported. A series of functional groups are tolerated in this reaction. Mechanistic studies support Zn alkynilides as intermediates in the reaction. This reaction protocol provides a practical method for the preparation of alkynylsilanes and expands the application of organometallic zinc in organic synthesis.
Tuning the Selectivity of AuPd Nanoalloys towards Selective Dehydrogenative Alkyne Silylation
Wissing, Maren,Studer, Armido
supporting information, p. 5870 - 5874 (2019/03/21)
The cross-dehydrogenative coupling of terminal alkynes and hydrosilanes catalyzed by AuPd nanoalloys is described. Metal nanoparticles are readily prepared in 15 minutes from commercially available and cheap starting materials by using a photochemical app
Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(i) N-heterocyclic carbene complexes
Thomas, Thomas J.,Merritt, Benjamin A.,Lemma, Betsegaw E.,McKoy, Adina M.,Nguyen, Tri,Swenson, Andrew K.,Mills, Jeffrey L.,Coleman, Michael G.
supporting information, p. 1742 - 1747 (2016/02/10)
Copper(i) N-heterocyclic carbene (CuNHC) complexes are more catalytically active than traditional transition metal salts for the cyclopropenation of internal alkynylsilanes and diazoacetate compounds. A series of 1,2,3-trisubstituted and 1,2,3,3-tetrasubstituted cyclopropenylsilane compounds were isolated in good overall yields. An interesting regioselective and chemodivergent reaction pathway was also observed to furnish a tetra-substituted furan for an electron-rich donor/acceptor diazoacetate. Finally, a practical synthesis of a cyclopropenyl-containing starting material that is useful for bioorthogonal chemistry is also described.
A novel synthesis of polysubstituted chromenes from various salicylaldehydes and alkynes under mild conditions
Tanaka, Kenta,Hoshino, Yujiro,Honda, Kiyoshi
supporting information, p. 2448 - 2450 (2016/05/19)
A novel synthesis of poly substituted chromenes from various salicylaldehydes and alkynes not having electron withdrawing substituents under mild conditions has been developed. The procedure is applicable for easily available various substituted salicylal
Rapid synthesis of crowded aromatic architectures from silyl acetylenes
Hein, Samuel J.,Arslan, Hasan,Keresztes, Ivan,Dichtel, William R.
supporting information, p. 4416 - 4419 (2015/01/08)
Congested aromatic systems were prepared by benzannulating silyl-protected arylacetylenes. The silyl groups may be retained in the naphthalene products and transformed into iodides in high yield. The desirable attributes of this strategy, particularly its remarkable tolerance of sterically hindered alkynes, are showcased in the efficient synthesis of a congested, branched oligo(naphthalene). As such, benzannulations of diaryl and silyl-protected acetylenes show outstanding promise for accessing new aromatic architectures.
Regioselective synthesis of multisubstituted benzenes by palladium-catalyzed intermolecular reaction of β-iodo-β-silylstyrenes with alkynes
Kinoshita, Hidenori,Takahashi, Hirotoshi,Miura, Katsukiyo
supporting information, p. 2962 - 2965 (2013/07/26)
The Pd-catalyzed reaction between β-iodo-β-silylstyrenes and terminal alkynes in i-Pr2NEt gave 1,2,3,5-tetrasubstituted benzenes with complete regioselection. The use of certain silylacetylenes as alkynes enabled efficient synthesis of 1,3,5-trissilyl-2-arylbenzenes, which could be transformed into other multisubstituted benzenes by displacement of the silyl groups.
Heterogeneously catalyzed aerobic cross-dehydrogenative coupling of terminal alkynes and monohydrosilanes by gold supported on oms-2
Yamaguchi, Kazuya,Wang, Ye,Oishi, Takamichi,Kuroda, Yoshiyuki,Mizuno, Noritaka
supporting information, p. 5627 - 5630 (2013/06/27)
Cross-dehydrogenative coupling of various terminal alkynes and monohydrosilanes efficiently proceeded in the presence of gold supported on OMS-2 (Au/OMS-2) using O2 as a terminal oxidant, affording the corresponding alkynylsilanes in moderate to high yields (see picture). The observed catalysis was truly heterogeneous, and the catalyst could be reused at least ten times without a significant loss of its high catalytic performance. Copyright
Copper- and base-free Sonogashira-type cross-coupling reaction of triarylantimony dicarboxylates with terminal alkynes under an aerobic condition
Wang, Xuan,Qin, Weiwei,Kakusawa, Naoki,Yasuike, Shuji,Kurita, Jyoji
experimental part, p. 6293 - 6297 (2010/01/18)
A simple copper- and base-free palladium-catalyzed Sonogashira-type cross-coupling by the use of triarylantimony dicarboxylates is described. Reaction of triarylantimony diacetates with terminal alkynes in the presence of 1 mol % of PdCl2(PPhs
