Density functional theory study of palladium‐catalyzed aryl‐nitrogen and aryl‐oxygen bond formation

Thomas R. Cundari; Jun Deng

doi:10.1002/poc.889

journal article Dec 15, 2004

Density functional theory study of palladium‐catalyzed aryl‐nitrogen and aryl‐oxygen bond formation

Thomas R. Cundari

Jun Deng

Journal of Physical Organic Chemistry Vol. 18 No. 5 pp. 417-425 · Wiley

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Abstract

AbstractA density functional theory study of the kinetics and thermodynamics of Pd‐phosphine‐catalyzed heteroatom bond formation $${\rm ArX} + {\rm REH}_n \mathrel{\mathop{\kern0pt\longrightarrow}\limits_{{\rm [Pd]}}} {\rm ArE}({\rm H})_{n - 1} {\rm R} + {\rm HX}$$ was carried out. Individual steps in the catalytic cycle—ArX oxidative addition, REHn coordination, HX loss and ArE(H)n−1R reductive elimination and β‐hydride elimination—were investigated. The effects of modification of the ligand (PH3 versus PMe3), leaving group (X = Cl versus X = Br), heteroatom substrate (REHn = H2O and NH3), aryl (Ar = phenyl, p‐cyanophenyl, p‐aminophenyl, pyridyl) and metal coordination number (Pd(PH3) versus Pd(PH3)2) were investigated. Copyright © 2004 John Wiley & Sons, Ltd.

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References

58

[1]

Hegedus LS (1999)

[2]

10.1021/cr9409804

[3]

10.1351/pac199668040779

[4]

10.1351/pac199971081539

[5]

Malleron JL (1997)

[6]

10.1016/s0022-328x(98)01063-8

[7]

10.1039/a827427z

[8]

10.1021/ar980063a

[9]

10.1021/cr9903048

[10]

10.1002/anie.198605081

[11]

10.1021/ja993446s

[12]

Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds

Norio. Miyaura, Akira. Suzuki

Chemical Reviews 10.1021/cr00039a007

[13]

10.1016/s0022-328x(98)01055-9

[14]

Buchwald SL Strem Chem. (2000)

[15]

10.1016/s0022-328x(98)01054-7

[16]

10.1021/ar9600650

[17]

10.1021/jo991699y

[18]

10.1021/ar970282g

[19]

10.1002/(sici)1521-3773(19980817)37:15<2046::aid-anie2046>3.0.co;2-l

[20]

10.1021/ja984321a

[21]

10.1021/ja9944599

[22]

10.1021/ja000094c

[23]

10.1021/jo990114x

[24]

10.1021/jo9700078

[25]

10.1039/a703043f

[26]

10.1021/jo971761w

[27]

A Rationally Designed Universal Catalyst for Suzuki–Miyaura Coupling Processes

Shawn D. Walker, Timothy E. Barder, Joseph R. Martinelli et al.

Angewandte Chemie International Edition 10.1002/anie.200353615

[28]

10.1021/ja00102a039

[29]

10.1351/pac199567020257

[30]

10.1002/anie.199501151

[31]

10.1021/om960860h

[32]

10.1021/ic951504e

[33]

10.1021/om9709190

[34]

10.1002/1522-2675(20011017)84:10<3043::aid-hlca3043>3.0.co;2-v

[35]

10.1016/s0040-4020(01)00350-7

[36]

10.1002/1521-3765(20010417)7:8<1703::aid-chem17030>3.0.co;2-k

[37]

10.1021/om049963n

[38]

10.1021/om034067h

[39]

10.1002/chem.200306056

[40]

10.1021/ja0315098

[41]

10.1016/s0040-4039(98)00398-0

[42]

10.1021/om030066d

[43]

10.1021/ja990309m

[44]

10.1021/jo000691h

[45]

10.1021/cr980452i

[46]

10.1002/9780470125823.ch2

[47]

10.1016/0010-8545(95)01133-1

[48]

Benson MT Rev. Comput. Chem. (1996) 10.1002/9780470125854.ch3

[49]

10.1021/cr980406i

[50]

Density-functional thermochemistry. III. The role of exact exchange

Axel D. Becke

The Journal of Chemical Physics 10.1063/1.464913

Showing 50 of 58 references

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Details

Published: Dec 15, 2004
Vol/Issue: 18(5)
Pages: 417-425
License: View

Authors

T

Thomas R. Cundari

Department of Chemistry, CASCaM, University of North Texas, Denton, Texas 76203, United States

J

Jun Deng

Cite This Article

Thomas R. Cundari, Jun Deng (2004). Density functional theory study of palladium‐catalyzed aryl‐nitrogen and aryl‐oxygen bond formation. Journal of Physical Organic Chemistry, 18(5), 417-425. https://doi.org/10.1002/poc.889

Density functional theory study of palladium‐catalyzed aryl‐nitrogen and aryl‐oxygen bond formation

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