By A. Togni, H. Grützmacher
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Extra resources for Catalytic Heterofunctionalization 2005
The reaction is accelerated in the presence of an electron-donating group, while a withdrawing group slows down the rate of coupling, the electronic effect of which is the reverse of the cross-coupling reactions of diborons and other organoboronic acids. The reaction proceeds through the formation of an (acetoxo)palladium(II) species (110) prior to transmetalation with diboron (Scheme 1-39). The presence of a base 33 34 1 Hydroboration, Diboration, Silylboration and Stannylboration O (pinBH) H-B O O X PdCl2(dppf)/Et3N (3 equivs) doxane/80 °C Y ArX (Ar=) H O Y Y ArX (X=) p-MeOC6H4 yield/% yield/% 77 77 81 83 79 43 77 84 79 80 16 11 12 nd 17 20 21 nd nd nd I Br OTf I I Br OTf I I p-ClCOC6H4 p-EtO2CC6H4 p-NO2C6H4 p-Me2NC6H4 2-iodothiophene Scheme 1-38 + B Borylation of Aryl Halides and Triflates such as KOAc is critical for the coupling reaction of diborons, suggesting a transmetalation mechanism occurring from Ar-Pd-OAc generated by displacement of X (109) with an acetate anion.
Per palladium) yields allenylboronate (23) as the major product. Thus, a double coordination of two C–C unsaturated bonds of enyne to a coordinate unsaturated catalyst affords 1,4-addition product. On the other hand, a monocoordination of an acetylenic triple bond to a rhodium(I)/bisphosphine complex leads to 24. Thus, asymmetric hydroboration of 1-buten-3-yne giving (R)-allenylboronate with 61% ee is carried out by using a chiral monophosphine (S)-(–)-MeOMOP (MeO-MOP=2-diphenylphosphino-2′-methoxy-1,1′-binaphthyl) .
Burgess, M. J. Ohmeyer, Chem. Rev. 1991, 91, 1179. (c) I. Beletskaya, A. Pelter, Tetrahedron, 1997, 53, 4957-5026. (d) G. C. Fu in Transition Metals for Organic Synthesis, M. Beller, C. ), Wiley-VCH, Weinheim, 1998, Vol. 2, 141-146. (e) T. Hayashi in Comprehensive Asymmetric Synthesis, E. N. Jacobsen, A. Pfaltz, H. ), Springer, Berlin, 1999, Vol. I, 351-366. 2 Reviews for diboration, silylboration, and stannylboration, see: (a) H. Wadepohl, Angew. Chem. Int. Ed. Engl. 1997, 36, 2441-2444. (b) H.