Preparation of para-Terphenylylalkanethiols with Different Chain Lengths

Abstract

Terphenylylalkanethiols with different chain length were synthesized using palladium-catalyzed cross-coupling reactions. While the thiols with two and three methylene groups were obtained via photoaddition of thiopivalic acid to the respective alkenes, the longer terphenylylalkanethiols were synthesized by two consecutive Kumada cross-coupling reactions followed by a Mitsunobu reaction for the introduction of the sulfur functionality.

cross-coupling - Mitsunobu reaction - self-assembly - thiols - arylations

References

<A NAME="RT10004SS-1">1</A> Flink S. van Veggel FCJM. Reinhoudt DN. Adv. Mater.  2000,  12:  1315 

<A NAME="RT10004SS-2">2</A> Dudek SP. Sikes HD. Chidsey CED. J. Am. Chem. Soc.  2001,  123:  8033 

<A NAME="RT10004SS-3">3</A> Lahiri J. Ostuni E. Whitesides GM. Langmuir  1999,  15:  2055 

<A NAME="RT10004SS-4">4</A> Pirrung MC. Angew. Chem. Int. Ed.  2002,  41:  1276 

<A NAME="RT10004SS-5">5</A> Xia Y. Whitesides GM. Angew. Chem. Int. Ed.  1998,  37:  550 

<A NAME="RT10004SS-6">6</A> Murgin T. Choong V. Maracas G. Langmuir  2000,  16:  5371 

<A NAME="RT10004SS-7">7</A> Xia Y. Whitesides GM. Ann. Rev. Mater. Sci.  1998,  28:  153 

<A NAME="RT10004SS-8">8</A> Slomon A. Cahen D. Lindsay S. Tomfohr J. Engelkes VB. Frisbie CD. Adv. Mater.  2003,  15:  1881 

<A NAME="RT10004SS-9">9</A> Wang W. Lee T. Reed MA. Phys. Rev. B  2003,  68:  35416 

<A NAME="RT10004SS-10">10</A> Himmel HJ. Terfort A. Wöll C. J. Am. Chem. Soc.  1998,  120:  12069 

<A NAME="RT10004SS-11">11</A> Cologne J. Buendia J. Sabadie J. Bull. Soc. Chim. Fr.  1967,  83:  4370 

<A NAME="RT10004SS-12">12</A> Drefahl G. Tahlmann K. J. Prakt. Chem.  1963,  20:  56 

<A NAME="RT10004SS-13">13</A> Quelet R. Bull. Soc. Chim. Fr.  1929,  45:  75 

<A NAME="RT10004SS-14">14</A> During this work, the synthesis of 11 using a somewhat different route was published: Ishida T. Mizutani W. Choi N. Akiba U. Fujihira M. Tokumoto H. J. Phys. Chem. B  2000,  104:  1680 

<A NAME="RT10004SS-15">15</A> Belmar J. Téllez J. Baeza J. Freer J. Z. Naturforsch., B: Chem. Sci.  2000,  55:  583 

<A NAME="RT10004SS-16">16</A> Volante RP. Tetrahedron Lett.  1981,  22:  3119 

<A NAME="RT10004SS-17">17</A> Mitsunobu O. Synthesis  1981,  1 

<A NAME="RT10004SS-18">18</A> Kulkarni SU. Patil VD. Heterocycles  1982,  18:  163 

<A NAME="RT10004SS-19">19</A> Brandsma L. Vasilevsky SF. Verkruijsse HD. Application of Transition Metal Catalysts in Organic Synthesis   Springer; Heidelberg: 1998. 

<A NAME="RT10004SS-20">20</A> Hayashi T. Mitsuo K. Makoto K. Tetrahedron Lett.  1979,  20:  1871 

<A NAME="RT10004SS-21">21</A> Nomura R. Miyazaki SI. Nakano T. Matsuda H. Chem. Ber.  1990,  123:  2081 

<A NAME="RT10004SS-22">22</A> Baldwin SW. Wilson JD. Aube J. J. Org. Chem.  1985,  50:  4432 

<A NAME="RT10004SS-23">23</A> Baldo MA. Chessa G. Marangoni G. Pitteri B. Synthesis  1987,  720