Abstract
Mono- and bifunctional fluorinated borate building blocks were prepared in three to
five steps with good to excellent overall yields. Compounds with both nucleophilic
and electrophilic functionalities are presented, which can be used for the anionic
derivatization of neutral molecules.
Key words
boron - fluorine - organometallic reagents - anions
References <A NAME="RT14007SS-1">1 </A>
Current address: Department of Chemistry, Imperial College, London, SW7 2AZ, UK.
2a </A>
Krossing I.
Raabe I.
Angew. Chem. Int. Ed.
2004,
43:
2066
2b </A>
Strauss SH.
Chem. Rev.
1993,
93:
927
<A NAME="RT14007SS-3">3 </A> For a review, see:
Chen EY.-X.
Marks TJ.
Chem. Rev.
2000,
100:
1391
4a </A>
Lightfoot A.
Schnider P.
Pfaltz A.
Angew. Chem. Int. Ed.
1998,
37:
2897
4b </A>
Roseblade SJ.
Pfaltz A.
Acc. Chem. Res., in press
4c </A>
Källström K.
Munslow I.
Andersson PG.
Chem. Eur. J.
2006,
12:
3194
4d </A>
Cui X.
Burgess K.
Chem. Rev.
2005,
105:
3272
4e </A>
Pfaltz A.
Blankenstein J.
Hilgraf R.
Hörmann E.
McIntyre S.
Menges F.
Schönleber M.
Smidt SP.
Wüstenberg B.
Zimmermann N.
Adv. Synth. Catal.
2003,
345:
33
<A NAME="RT14007SS-5">5 </A>
Kündig EP.
Saudan CM.
Bernardinelli G.
Angew. Chem. Int. Ed.
1999,
38:
1219
<A NAME="RT14007SS-6">6 </A>
Massey AG.
Park AJ.
J. Organomet. Chem.
1964,
2:
245
<A NAME="RT14007SS-7">7 </A>
Nishida H.
Takada N.
Yoshimura M.
Sonoda T.
Kobayashi H.
Bull. Chem. Soc. Jpn.
1984,
57:
2600
8a </A>
van den Broeke J.
de Wolf E.
Deelman B.-J.
van Koten G.
Adv. Synth. Catal.
2003,
345:
625
8b </A>
van den Broeke J.
Deelman B.-J.
van Koten G.
Tetrahedron Lett.
2001,
42:
8085
8c </A>
van den Broeke J.
Lutz M.
Kooijman H.
Spek AL.
Deelman B.-J.
van Koten G.
Organometallics
2001,
20:
2114
8d </A>
Jia L.
Yang X.
Ishihara A.
Marks TJ.
Organometallics
1995,
14:
3135
9a </A> For R = Me, see:
Carpentier J.-F.
Wu Z.
Lee CW.
Strömberg S.
Christopher JN.
Jordan RF.
J. Am. Chem. Soc.
2000,
122:
7750
9b </A> For R = n -Bu, see:
Döring S.
Erker G.
Fröhlich R.
J. Organomet. Chem.
2002,
643-644:
61
9c </A> For R = Me, Et, i -Pr and CH2 C(CH3 )3 , see:
Bavarian N.
Baird MC.
Organometallics
2005,
24:
2889
<A NAME="RT14007SS-10">10 </A>
Hewavitharanage P.
Danilov EO.
Neckers DC.
J. Org. Chem.
2005,
70:
10653
11a </A>
Smidt SP.
Zimmermann N.
Studer M.
Pfaltz A.
Chem. Eur. J.
2004,
10:
4685
11b </A>
Blackmond DG.
Lightfoot A.
Pfaltz A.
Rosner T.
Schnider P.
Zimmermann N.
Chirality
2000,
12:
442
<A NAME="RT14007SS-12">12 </A>
Robson MJ, and
Williams J. inventors; Brit. UK Pat. Appl. GB 2171994.
; Chem. Abstr. 1987 , 107 , 2700
<A NAME="RT14007SS-13">13 </A>
Wang C.
Erker G.
Kehr G.
Wedeking K.
Froehlich R.
Organometallics
2005,
24:
4760
<A NAME="RT14007SS-14">14 </A> For the DFT-optimized [BP86/SV(P)] molecular structure of [B(C6 F6 )4 ]- , see the supporting information of:
Krossing I.
Raabe I.
Chem. Eur. J.
2004,
10:
5017
15a </A> B(ArF )3 was only isolated as a pyrolysis product of a platinum complex, see:
Konze WV.
Scott BL.
Kubas GJ.
Chem. Commun.
1999,
1807
15b </A> For the pyridine adduct B(ArF )3 ·py, see:
Bourke SC.
MacLachlan MJ.
Lough AJ.
Manners I.
Chem. Eur. J.
2005,
11:
1989
16a </A>
Molander GA.
Ellis N.
Acc. Chem. Res.
2007,
40:
275
16b </A>
Darses S.
Genet J.-P.
Eur. J. Org. Chem.
2003,
4313
17a </A>
Ito T.
Iwai T.
Mizuno T.
Ishino Y.
Synlett
2003,
1435
17b </A>
Frohn H.-J.
Franke H.
Fritzen P.
Bardin VV.
J. Organomet. Chem.
2000,
598:
127
<A NAME="RT14007SS-18">18 </A>
Molander GA.
Katona BW.
Machrouhi F.
J. Org. Chem.
2002,
67:
8416
<A NAME="RT14007SS-19">19 </A> For a review, see:
Knochel P.
Dohle W.
Gommermann N.
Kneisel FF.
Kopp F.
Korn T.
Sapountzis I.
Vu VA.
Angew. Chem. Int. Ed.
2003,
42:
4302
<A NAME="RT14007SS-20">20 </A>
Purification of Laboratory Chemicals
3rd ed.:
Perrin DD.
Armarego WLF.
Pergamon;
Oxford:
1988.
<A NAME="RT14007SS-21">21 </A>
Gottlieb HE.
Kotlyar V.
Nudelman A.
J. Org. Chem.
1997,
62:
7512
