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3 C-C Bond Formation: Cross-coupling Reaction of rganometal Compounds with rganic alids M C-m + X-C C-C + m-x 12ew-2 m : metal (Li, Mg, Zn, Al, Si, Sn, g, Zr) (B: not used) X : halogen (I, Br, ) M : transition metal Suzuki Coupling Using rganoboron Compounds: C B + X-C Pd base C-C
4 T. J. Colacot, Platinum Metals Rev., 2011, 55, !
5 -24 B + X Pd cat base (1979) B + Pd cat X (1980) base Pd cat B + X (1981) base B X Pd cat + (1985) base B B X Pd cat + (1992) base Fu X Pd cat + Soderquist and (base) Fürstner 1995
6 -4 X X R' R (trans trans) R BY 2 Pd R' X R' R base (trans, trans) 2 R R' (trans, cis) X R' R R' BY 2 R X Pd R (cis, trans) X R' R base R' (cis, cis)
7 -7 1-Alkenylborane 1-Alkenyl Bromide Yield (%) Product [Purity (%)] Bu Br Ph Ph B b) 86 [98] Bu Bu B a) Bu Br Ph Ph 49 [99] Bu B a) Br Ph Bu Ph 42 [89] Bu Bu B B b) Br ex ex Bu 88 [99] a) Br ex Bu ex 49 [98] Ph Ph B b) 89 [98] Br Ph Ph Reaction conditions: 1-3 mol % of Pd(PPh 3 ) 4 / aet / Benzene / Reflux 2h a) Disiamyl b) 1,3,2-Benzodioxaboryl
8 2 Me Me Me Me Me "Palytoxin" " C (MW ) 6) Me Me Synthesis: Kishi et al., J. Am. Chem. Soc, 1989, 111, 7525,
9 U-19 Cross-Coupling of 1-Alkenylboranes with Aryl, Allyl, Benzyl, and Alkynyl alides a) 1-Alkenylborane b) alide Product c) Yield (%) Bu B PhI Bu Ph 100 PhBr Bu Ph 98 Ph Bu Ph Br Bu CEt CEt 87 Br Bu
10 -13 I + B C 8 17 Pd 2 (dppf) (3 mol%) ame / TF, reflux C % Br + B Pd 2 (dppf) (3 mol%) ame / TF, reflux 88 % Br + B (C 2 ) 3 Me (C 2 2) 3 Me Me Me 87 % Br + B C 8 17 Pd 2 (dppf) (3 mol%) ame / TF, reflux C %
11 Suzuki Coupling: -17 R B() 2 + X R Pd(0), base R R R B() 2 + X R' Pd(0), base R R' Ullmann Reaction: R R R X + X R' Cu, high temp. R R' R' R'
12 Angiotensin II Receptor Antagonist t (Losartan) CPh 3 CPh 3 C BuLi Br 2. B(Pr i ) B() 2 3 Pd(Ac) 2 / 3 PPh 3 3. IPA- 4 aq. K 2 C 3-2 TF / DME 90% reflux 93% CPh 3-19 C 4 9 Merck, J. rg. Chem. 59, 6391 (1994) Losartan (Antihypertensive)
13 Suzuki coupling is a shortcut to biaryls (ovartis's s Valsartan Process) -18 C 3 C 3 C 3 C 3 C PRE-SUZUKI RUTE C 5 Synthetic steps C Valsartan (Antihypertensive) 1 Step SUZUKI RUTE 3.5 million users in Japan 22 million users in the whole world C + () 2 B
14 Glivec /Tasigna anticancer drugs synthesis by Suzuki-coupling Imatinib(Glivec, ovartis) ilotinib(tasigna, ovartis) 6 Presentation Title Presenter ame Date Subject Business Use nly
15 Useful drugs synthesis by Suzuki coupling #IV* rg. Proc. Res. Dev. 2002, 6, 323. #'() Angew. Chem. Int. Ed. 2005, 44, Atazanavir (Reyataz, ovartis) Vancomycin(Eli Lilly)!"#$%& J. Comb. Chem. 2003, 5, 118. Celecoxib(Celebrex, Searle) 7 Presentation Title Presenter ame Date Subject Business Use nly
16 Boscalid; Agrochemicals (BASF, Germany) () 2 B Boscalid Multi-purpase Fungicide for Specialty Crops
17 Bayer's "Bixafen" Production (Agrochemical): multi-100-tons B + Br F Pd(acac) 2 [P(t-Bu) 3 ]BF 4 a 2 C 3 Bu/water 60 C F F 2 C F Ac Bixafen
18 Liquid crystal: -22 Chisso (Japan) C 5 11 B() 2 + I F 5 11 ( ) 2 F F LC Glass substrate Pd catalyst / base C 5 11 F F Merck (Germany) F F F F R CF 3 C 3 7 CF 3 F
19 Applications of Suzuki Coupling : LED Materials(1) Si IDEMITSU (Fluorescent Material) TS (ole Transporting Material)
20 U-36 Synthesis of Poly(ortho-phenylenes) Pd(PPh 3 ) 4 / Ba() 2 Br DME- 2, reflux B() 2 helical structure. S. Simpkins et al., Tetrahedron Lett., 1998, 39, 9093
21 Applications of Suzuki Coupling : LED Materials(3) C 8 C 8 C 8 C 8 S n n C 8 C 8 C 2 Me C 2 Me n SUMITM CEMICAL (Polymer-type Materials)
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