Thiophene synthesis via 1,1-carboboration.

Reaction of bis(tert-butylethynyl)sulfide with the boron Lewis acid reagents X-B(C6F5)2 (X = CH3, Cl, C6F5) in pentane at r.t. gave the respective borylated thiophenes in a sequence of 1,1-carboboration reactions. In contrast, bis(phenylethynyl)sulfide reacted with B(C6F5)3 only in a 2 : 1 molar ratio to give a benzothiophene derivative.

[1]  G. Erker,et al.  Reactions of Boroles Formed by 1,1-Carboboration , 2015 .

[2]  G. Erker,et al.  Preparation of dithienylphospholes by 1,1-carboboration. , 2014, Chemistry.

[3]  B. Wrackmeyer,et al.  Selective Synthesis of Stannoles by 1,1‐Carboboration of Bis(trimethylsilylethynyl)tin Compounds Using Weakly and Strongly Electrophilic Triorganoboranes: Characterization of a Zwitterionic Intermediate , 2014 .

[4]  A. Heeger,et al.  Silaindacenodithiophene-based molecular donor: morphological features and use in the fabrication of compositionally tolerant, high-efficiency bulk heterojunction solar cells. , 2014, Journal of the American Chemical Society.

[5]  G. Erker,et al.  Borole formation by 1,1-carboboration. , 2014, Journal of the American Chemical Society.

[6]  Feng Xu,et al.  One‐Pot Preparation of Arylethynyl Sulfides and Bis(arylethynyl) Sulfides , 2013 .

[7]  G. Erker,et al.  Facile 1,1-Carboboration Reactions of Acetylenic Thioethers , 2013 .

[8]  Klaus Müllen,et al.  Design strategies for organic semiconductors beyond the molecular formula. , 2012, Nature chemistry.

[9]  S. Yamaguchi,et al.  Polycyclic π-electron system with boron at its center. , 2012, Journal of the American Chemical Society.

[10]  G. Erker,et al.  The 1,1-carboboration of bis(alkynyl)phosphanes as a route to phosphole compounds. , 2012, Angewandte Chemie.

[11]  G. Erker,et al.  1,1-Carboboration. , 2012, Chemical communications.

[12]  S. Yamaguchi,et al.  Thiophene-fused ladder boroles with high antiaromaticity. , 2011, Journal of the American Chemical Society.

[13]  G. Bazan,et al.  Lewis acid adducts of narrow band gap conjugated polymers. , 2011, Journal of the American Chemical Society.

[14]  R. Fröhlich,et al.  1,1-carboboration of 1-alkynes: a conceptual alternative to the hydroboration reaction. , 2011, Organic letters.

[15]  R. Fröhlich,et al.  Exploring the limits of frustrated Lewis pair chemistry with alkynes: detection of a system that favors 1,1-carboboration over cooperative 1,2-P/B-addition. , 2010, Chemistry, an Asian journal.

[16]  R. Fröhlich,et al.  Carbon-carbon bond activation by 1,1-carboboration of internal alkynes. , 2010, Journal of the American Chemical Society.

[17]  R. McDonald,et al.  Divergent Reactivity of Perfluoropentaphenylborole with Alkynes , 2010 .

[18]  B. Wrackmeyer,et al.  Fused Silacarbacycles Containing a Silole Unit: 1,2‐Hydroboration and 1,1‐Organoboration of Alkynyl(vinyl)silanes , 2010 .

[19]  R. Fröhlich,et al.  Photochemical isomerisation of boryl-substituted silole derivatives. , 2010, Chemical communications.

[20]  O. Blacque,et al.  Activation of Terminal Alkynes by Frustrated Lewis Pairs , 2010 .

[21]  K. Mori,et al.  A B-B bond-containing polycyclic pi-electron system: dithieno-1,2-dihydro-1,2-diborin and its dianion. , 2009, Journal of the American Chemical Society.

[22]  R. Fröhlich,et al.  Reaction of Bis(alkynyl)silanes with Tris(pentafluorophenyl)borane: Synthesis of Bulky Silole Derivatives by Means of 1,1‐Carboboration under Mild Reaction Conditions , 2009 .

[23]  B. Wrackmeyer.  Metallacyclopentadienes and related heterocycles via 1,1‐organoboration of alkyn‐1‐ylmetal compounds , 2006 .

[24]  R. Fröhlich,et al.  Synthesis, structural features, and formation of organometallic derivates of C1-bridged Cp/amido titanium and zirconium CpCN-constrained geometry systems , 2005 .

[25]  Samuel A. Johnson,et al.  Regioselective coupling of pentafluorophenyl substituted alkynes: mechanistic insight into the zirconocene coupling of alkynes and a facile route to conjugated polymers bearing electron-withdrawing pentafluorophenyl substituents. , 2003, Journal of the American Chemical Society.

[26]  B. Wrackmeyer,et al.  Novel titana-2,4-cyclopentadienes by 1,1-alkylboration , 2002 .

[27]  G. Kehr,et al.  Reactions of zwitterionic η2-(alkyn-1-yl-borate)alkenyltin compounds with Lewis bases , 1999 .

[28]  D. Parks,et al.  Synthesis, Properties, and Hydroboration Activity of the Highly Electrophilic Borane Bis(pentafluorophenyl)borane, HB(C6F5)21 , 1998 .

[29]  B. Wrackmeyer.  1,1-organoboration of alkynylsilicon, -germanium, -tin and -lead compounds , 1995 .

[30]  B. Wrackmeyer,et al.  Stabilization of Triorganotin Cations — Competition between Intramolecular Coordinative O, S or NSn Bonds and Side‐on π Coordination to CC Bonds , 1994 .

[31]  G. Kehr,et al.  1,1‐Organoboration of Di‐1‐alkynylsilanes with Alkynyl Groups of Different Reactivity: New Organometallic‐Substituted Siloles , 1993 .

[32]  B. Wrackmeyer,et al.  Routes to Stannoles, Stannolenes and 1‐Stanna‐4‐bora‐2,5‐cyclohexadienes – Crystal Structure of a Triorganotin Cation Stabilized by π1‐Coordination , 1993 .

[33]  G. Kehr,et al.  Organosubstituierte 1,1′‐Spirobisilole und 1,1′‐Spirobigermole durch vierfache Organoborierung von Tetra‐1‐alkinylsilanen und ‐germanen , 1993 .

[34]  B. Wrackmeyer,et al.  Organo‐substituierte Silole durch zweifache Organoborierung von Di‐1‐alkinylsilanen , 1993 .

[35]  A. Sebald,et al.  Organotin cations stabilized by π coordination – synthesis and NMR studies in solution and in the solid state , 1992 .

[36]  G. Kehr,et al.  π-Coordination of Diorganotin Dications† , 1991 .

[37]  B. Wrackmeyer,et al.  Triorganolead Cations Stabilized by Size‐on Coordination to the CC Bond in Alkynylborates , 1989 .

[38]  A. Sebald,et al.  Organoboration of cis-diethynylplatinum(II) complexes with R2P(CH2)2PR2 ligands: Platinacyclopentadienes and their behaviour in solution , 1986 .

[39]  A. Sebald,et al.  Synthesis of platinacyclopentadienes via organoboration of cis-platinum(II) acetylides , 1983 .

[40]  A. Massey,et al.  Perfluorophenyl derivatives of the elements : I. Tris(pentafluorophenyl)boron , 1964 .