A One-Pot Method for the Synthesis of Phenylalkynyl-Substituted Terminal Alkynes by Deprotection/Stannylation followed by a Migita–Kosugi–Stille coupling

A practical one-pot approach for the synthesis of arylalkynyl-substituted terminal alkynes has been developed through a deprotection/ stannylation of a phenylethynyl phosphine oxide followed by Migita–Kosugi–Stille coupling, avoiding the longer synthetic route involving repeated deprotection/Sonogashira coupling. Other features of this approach include mild reaction conditions, excellent yields, facile isolation of products and wide functional group tolerance.

[1]  C. Meier,et al.  Insights into the gold-catalyzed propargyl ester rearrangement/tandem cyclization sequence: radical versus gold catalysis-Myers-Saito- versus Schmittel-type cyclization. , 2015, Chemistry.

[2]  Hui Wang,et al.  Organogels formed by substituent-free pyrene-appended oligo(m-phenylene ethynylene)s. , 2015, Chemical communications.

[3]  A. Orita,et al.  Selective Deprotection of Me3Si-/Ph2P(O)-protected Arylalkynes: Methyl Grignard Reagent-promoted Dephosphorylation of Ph2P(O)-protected Alkynes , 2014 .

[4]  A. Orita,et al.  One-pot transformation of Ph2P(O)-protected ethynes: deprotection followed by transition metal-catalyzed coupling. , 2013, The Journal of organic chemistry.

[5]  Philip M. Byers,et al.  Polyaromatic ribbon/benzofuran fusion via consecutive endo cyclizations of enediynes. , 2012, Organic letters.

[6]  F. Rominger,et al.  Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes , 2012 .

[7]  A. Orita,et al.  Synthesis and Properties of 9,10-Anthrylene-substituted Phenyleneethynylene Dyes for Dye-sensitized Solar Cell , 2011 .

[8]  Pengcheng Huang,et al.  A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols , 2011, Beilstein journal of organic chemistry.

[9]  C. Adachi,et al.  Fluoro-substituted Phenyleneethynylenes: Acetylenic n-Type Organic Semiconductors , 2010 .

[10]  C. Nájera,et al.  The Sonogashira reaction: a booming methodology in synthetic organic chemistry. , 2007, Chemical reviews.

[11]  Zheng,et al.  Stereoselective total synthesis of (3R,8S)-falcarindiol, a common polyacetylenic compound from umbellifers , 1999, Journal of natural products.

[12]  Haji,et al.  First total synthesis of optically active panaxydol, a potential antitumor agent isolated from Panax ginseng , 1998 .

[13]  J. Herbert,et al.  TRANSITION METAL PROMOTED ACETYLENE ISOMERISATION REACTIONS IN ORGANIC SYNTHESIS : A SYNTHESIS OF (+)-(4S,5S) : MURICATACIN , 1995 .

[14]  S. Shim,et al.  Photocycloaddition reaction of some conjugated hexatriynes with 2,3-dimethyl-2-butene , 1988 .