Consecutive Palladium Catalyzed Reactions in One-Pot Reactions

Author:

Vaaland Ingrid Caroline1,Sydnes Magne Olav1

Affiliation:

1. Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, NO-4036 Stavanger, Norway

Abstract

Combining palladium catalyzed reactions in one-pot reactions represents an efficient and economical use of catalyst. The Suzuki-Miyaura cross-coupling has been proven to be a reaction which can be combined with other palladium catalyzed reactions in the same pot. This mini-review will highlight some of the latest examples where Suzuki-Miyaura cross-coupling reactions have been combined with other palladium catalyzed reactions in one-pot reaction. Predominantly, examples with homogeneous reaction conditions will be discussed in addition to a few examples from the authors where Pd/C have been used as a catalyst.

Funder

The University of Stavanger

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

Reference58 articles.

1. Miyaura,N.; Suzuki, A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the OR Br B(MIDA) Pd(OAc). 2 (10 mol%),XPhos (20 mol%),K3 PO 4 (3.0 equiv, THF,65 o C OR (HO) 2 B B(MIDA) OR OMOM MeO CO2 Me Pd(OAc) 2 (10 mol%),SPhos (20 mol%),K3 PO 4 (7.5 equiv, dioxane/H2 O,65 o C MeO CO2 Me Br 70% R = MOM79% R = Me1) NH 3 (10 equiv),AlMe3 (20 equiv),toluene, 0-80 o C2) HCl, MeOH, rt OH MeO CO2 NH2 dictyoterphenyl A51% yield over two stepsOH R = MOM or Me R = MOMOR OR BBr3, CH 2 Cl2,-78 o C-rtR = Me OH MeO CO2 H dictyoterphenyl B78%OH O O B O O N MeB(MIDA) MeO MeO P SPhos N Br (HO) 2 B H3 N Cl + NH N PdCl 2 (dppf),K 2CO3, EtOH/H 2O (5:1),MW sealed tube, 60 oC,4 hPdCl 2 (dppf) (additional),IMes, H 2O2, AcOH, MW sealed tub, 118 oC,18 min 32% N N Isocryptolepine NN IMes presence of palladium catalyst, J. Chem. Soc. Chem. Commun. 1979,19,135-152. http://dx.doi.org/10.1039/c39790000866

2. Miyaura,N.; Yamada,K.; Suzuki, A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett. 1979,20,3437-3440. http://dx.doi.org/10.1016/S0040-4039(01) 95429-2

3. Miyaura,N.; Suzuki, A. Palladium-catalyzed cross-coupling reac-tions of organoboron compounds. Chem. Rev. 1995,95,2457-2483. http://dx.doi.org/10.1021/cr00039a007

4. Miyaura.; N. Cross-coupling reaction of organoboron compounds via base-assisted transmetalation to Palladium(II) complexes, J. Organomet. Chem. 2002,653,54-57. http://dx.doi.org/10.1016/S0022-328X(02) 01264-0

5. Suzuki.; A. Cross-coupling reactions via organoboranes, J. Organ-omet. Chem. 2002,653,83-90. http://dx.doi.org/10.1016/S0022-328X(02) 01269-X

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