Use of cheaper metal than Rh, CHCl3-free Pd catalyst, in 1,2-addition of aromatic aldehydes with arylboronic acids

Suzuki, Kiyoto; Arao, Takafumi; Ishii, Satoru; Maeda, Yuka; Kondo, Kazuhiro; Aoyama, Toyohiko

doi:10.1016/j.tetlet.2006.05.184

Cited by 61 publications

(11 citation statements)

References 21 publications

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“…In 2005 Carreira and co-workers disclosed a Rh/dienecatalyzed enantioselective conjugate addition of arylboronic acids to enals, a traditionally challenging class of acceptor. [74] Although 1,2-addition of boronic acids to aldehydes has been studied extensively, [75] a general, reliable enantioselective conjugate addition protocol was lacking. This might be attributed to the fact that any effort could be thwarted by a 1,2-addition either in competition with (to give 132 instead of 130) or after the 1,4-addition (further reaction of 130 to give 131; Scheme 33).…”

Section: Rhodium/diene-catalyzed Asymmetric Conjugate Addition Of Arymentioning

confidence: 99%

Chiral Olefins as Steering Ligands in Asymmetric Catalysis

2008

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Metal-catalyzed asymmetric processes offer one of the most straightforward ways to introduce stereogenic centers. Hence, the development of novel chiral ligands that can effectively induce asymmetry in reactions is crucial in modern organic synthesis. While many established chiral ligands bind to a metal through heteroatoms, structures that coordinate to metals through carbon atoms have received little attention so far. Here, we highlight the increasing number of such chiral chelating olefin ligands as well as their application in a variety of metal-catalyzed transformations.

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Section: Rhodium/diene-catalyzed Asymmetric Conjugate Addition Of Arymentioning

confidence: 99%

Chiral Olefins as Steering Ligands in Asymmetric Catalysis

2008

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“…Insertion of the C-O double bond into a late transition metal-carbon bond is rare compared to that of C-C double bonds, but it was well established by Hartwig in a stoichiometric insertion of aldehydes into arylrhodium(I) complexes. 65 Palladium(II) complexes of tris(1-naphth- yl)phosphine (63, entry 1 of the table in Scheme 13), 37 JohnPhos (64, entry 2), 42 tol-binap (entry 3), 35 N-heterocyclic carbene 65 (NHC, entry 3), 40,41 and phosphiniteand phosphite-based palladacycles 26 and 27 (entries 5-7), 28,29,32 as well as a cationic bipyridyl complex 66 (entry 8) 38 catalyze arylation of aldehydes in the presence of a base (Scheme 13). It is remarkable that palladacycle 27a catalyzes the addition at room temperature for both aromatic and aliphatic aldehydes.…”

Section: Addition To Aldehydesmentioning

confidence: 99%

“…12 Although these precedents suffered from competitive Heck coupling and low catalyst efficiency, we found that dicationic [Pd(dppe)(PhCN) 2 ]X 2 (X = BF 4 , SbF 6 ) is a selective catalyst for 1,4-additions of ArB(OH) 2 , [13][14][15][16][17][18][19][20] ArBF 3 K, 21 ArSi(OR) 3 , 22 ArSiF 3 , and Ar 4 Bi 23 to unsaturated carbonyl compounds in an aqueous medium. This review focuses on such 1,4-additions of arylboronic acid [ArB(OH) 2 ] to electron-deficient alkenes and their enantioselective versions, and related chemistry reported in Grignard-type additions of arylboronic acid to aldehydes, 28,29,32,[34][35][36][37][38][39][40][41][42][43] imines, 29,44 and nitriles. 45,46 2…”

Section: Introductionmentioning

confidence: 99%

“…phosphine (63, entry 1 of the table in Scheme 13),37 JohnPhos (64, entry 2), 42 tol-binap (entry 3),35 N-heterocyclic carbene 65 (NHC, entry 3),40,41 and phosphiniteand phosphite-based palladacycles 26 and 27 (entries 5-7),28,29,32 as well as a cationic bipyridyl complex 66 (entry 8)38 catalyze arylation of aldehydes in the presence of a base (Scheme 13). It is remarkable that palladacycle 27a catalyzes the addition at room temperature for both aromatic and aliphatic aldehydes.…”

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confidence: 99%

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Celebrating 20 Years of SYNLETT - Special Account On Palladium(II)-Catalyzed Additions of Arylboronic Acids to Electron-Deficient Alkenes, Aldehydes, Imines, and Nitriles

Miyaura¹

2009

Synlett

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P a l l a d i u m ( I I ) -C a t a l y z e d A d d i t i o n R e a c t i o n s Norio MiyauraAbstract: The enantioselective synthesis of cyclic and acyclic b-aryl ketones, esters, and amides by palladium(II)-catalyzed 1,4-addition of an arylboronic acid or a potassium aryltrifluoroborate to unsaturated carbonyl compounds is described. The protocol provides simple access to biologically and pharmaceutically active compounds such as optically active chromenes, (R)-tolterodine, (R)-CDP 840, and the endothelin receptor antagonist. The palladium(II) catalysts are also efficient for Grignard-type addition of arylboronic acids to carbon-heteroatom double bonds and triple bonds of aldehydes, ketones, aldimines, and nitriles. The catalytic cycle involves transmetalation between arylboronic acid and palladium(II) complexes as the key process, the mechanism of which is discussed on the basis of characterization of the transmetalation intermediates and electronic effects of the substituents. The enantioselection mechanism and the efficiency of a chiraphos ligand for structurally planar unsaturated ketones are discussed on the basis of the results of DFT computational studies on the modes of coordination of the substrates to the phenylpalladium(II)/(S,S)-chiraphos intermediate. This review focuses mainly on reactions of arylboronic acids; there are very few such reports for other organoboronic acids or esters, but pinacol allylboronate undergoes 1,4-addition to unsaturated N-acylpyrroles.

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“…[4] Kondo and Aoyama reported the Pd(OAc) 2 /tol-binap complex as a chloroform-free catalyst. [5] Hu proposed anionic palladacycles for the 1,2-addition of arylboronic acids to aromatic and aliphatic aldehydes at room temperature. [6] More recently, Shirai and Kuriyama described efficient 1,2-addition reactions of aryl-, heteroaryl-, and alkenylboronic acids to aromatic, heteroaromatic, and aliphatic aldehydes catalyzed 5692 acids.…”

Section: Introductionmentioning

confidence: 99%