57951-69-6Relevant academic research and scientific papers
Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation
Zhang, Yanchen,Yu, Bangkui,Gao, Binjian,Zhang, Tianze,Huang, Hanmin
supporting information, (2019/01/21)
A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under
Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation
Zhang, Yanchen,Yu, Bangkui,Gao, Binjian,Zhang, Tianze,Huang, Hanmin
supporting information, p. 535 - 539 (2019/01/24)
A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under
E-Selective dimerization of phenylacetylene catalyzed by cationic tris(μ-hydroxo)diruthenium(II) complex and the mechanistic insight: The role of two ruthenium centers in catalysis
Kiyota, Sayori,Soeta, Hirofumi,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi
, p. 419 - 428 (2016/12/16)
A dinuclear complex [(Me3P)3Ru(μ-OH)3Ru(PMe3)3]+[OPh]? (1) (0.5 mol%) catalyzes E-selective dimerization of phenylacetylene, which involves the C–H bond cleavage of phenylacetyle
Highly Enantioselective Bromocyclization of Allylic Amides with a P/P=O Double-Site Lewis Base Catalyst
Kawato, Yuji,Ono, Hiromi,Kubota, Akino,Nagao, Yoshihiro,Morita, Naoki,Egami, Hiromichi,Hamashima, Yoshitaka
supporting information, p. 2127 - 2133 (2016/02/09)
The enantioselective bromocyclization of allylic amides catalyzed by phosphorus-containing Lewis bases was examined in detail. A series of control experiments and NMR studies showed that a partially oxidized bis-phosphine generated in situ serves as the a
A Trialkylphosphine-Derived Palladacycle as a Catalyst in the Selective Cross-Dimerization of Terminal Arylacetylenes with Terminal Propargyl Alcohols and Amides
Lauer, Matthew G.,Headford, Benjamin R.,Gobble, Olivia M.,Weyhaupt, Michelle B.,Gerlach, Deidra L.,Zeller, Matthias,Shaughnessy, Kevin H.
, p. 5834 - 5842 (2016/09/09)
A method for the selective cross-dimerization of terminal aryl alkynes with propargyl alcohols to afford linear (E)-enynol products is reported. The complex [Pd(μ-κ2-O,O-OAc)(κ2-C,P-(t-Bu)2PCH2C(Me)2CH2)]2 selectively affords (E)-5-aryl-2-en-4-yn-1-ol products in good yields under mild conditions with high chemo-, regio-, and stereoselectivity. In contrast, previously reported examples of this reaction afford the branched 4-aryl-2-hydroxymethanol-1-buten-3-yne. Propargyl amides are also selectively cross-dimerized, but with lower regioselectivity for the linear enyne. The method has been applied to the synthesis of (E)-5-phenyl-2-penten-4-yn-1ol, which is a precursor to type 2 diabetes drug candidate NNC 61-4655, in 72% yield from phenylacetylene and propargyl alcohol. The palladacycle precatalyst reacts with aryl alkynes to afford the first example of a dimeric palladacycle complex with a μ-κ2-C1,C1-bound acetylide ligand. This complex is observed during the catalytic reaction and is a competent precatalyst.
Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes
Xu, Hua-Dong,Zhang, Ren-Wei,Li, Xiaoxun,Huang, Suyu,Tang, Weiping,Hu, Wen-Hao
supporting information, p. 840 - 843 (2013/03/29)
Cross-dimerization of terminal arylacetylenes and terminal propargylic alcohols/amides has been achieved in the presence of a rhodium catalyst. This method features high chemo- and regioselectivities rendering convenient and atom economical access to functionalized enynes.
Facile access to 2,5-disubstituted-4-chloromethyl-3-iodofuran derivatives via ICl-mediated cyclization of 1-alkyl-2-alkynylallylic alcohols
Thongsornkleeb, Charnsak,Rabten, Wangchuk,Ruchirawat, Somsak,Bunrit, Anon,Tummatorn, Jumreang
supporting information, p. 6615 - 6619,5 (2012/12/11)
Substituted furans are conveniently synthesized from acyclic secondary 1-alkyl-2-alkynylallylic alcohol precursors via an ICl-promoted cyclization reaction. The furans generated by this method incorporate both iodine and chlorine atoms which may be useful for further elaborations via many known methods. The methodology is suitable for generating a wide array of furan products which can serve as useful building blocks for the synthesis of various biologically active molecules.
Facile access to 2,5-disubstituted-4-chloromethyl-3-iodofuran derivatives via ICl-mediated cyclization of 1-alkyl-2-alkynylallylic alcohols
Thongsornkleeb, Charnsak,Rabten, Wangchuk,Bunrit, Anon,Tummatorn, Jumreang,Ruchirawat, Somsak
supporting information, p. 6615 - 6619 (2013/01/15)
Substituted furans are conveniently synthesized from acyclic secondary 1-alkyl-2-alkynylallylic alcohol precursors via an ICl-promoted cyclization reaction. The furans generated by this method incorporate both iodine and chlorine atoms which may be useful for further elaborations via many known methods. The methodology is suitable for generating a wide array of furan products which can serve as useful building blocks for the synthesis of various biologically active molecules.
Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes
Hashmi, A. Stephen K.,Rudolph, Matthias,Rominger, Frank
supporting information; experimental part, p. 667 - 671 (2011/03/22)
Various 2-alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold-catalyzed transformation was investigated. The use of AuI catalysts bearing carbene ligands, of either the N-heterocyclic carbene or nitrogen acyclic carbene type, delivered the desired products with low catalyst loadings and under very mild reaction conditions. A broad array of substrates was tested, including alkyl-, alkenyl-, and aryl-substituted alkynes, as well as substrates with two alkynyl moieties. The methodology turned out to have a broad scope. Secondary allyl alcohols were also tolerated, and the resulting trisubstituted furans could be isolated in high yields. Easily accessible 2-alkynylallyl alcohols were transformed into highly substituted furans under very mild reaction conditions by the use of gold(I)-carbene catalysts. A broad range of substrates could be transformed in high yields and within short reaction times.
Synthesis of 1,3-enynes via Suzuki-type reaction of vinylic tellurides and potassium alkynyltrifluoroborate salts
Stefani, Hélio A.,Cella, Rodrigo,D?rr, Felipe A.,Pereira, Claudio M.P.,Zeni, Gilson,Gomes Jr., Marlito
, p. 563 - 567 (2007/10/03)
The palladium-catalyzed cross-coupling reaction between potassium alkynyltrifluoroborate salts and vinylic tellurides proceeds readily to afford 1,3-enynes with moderate to good yields.
