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Synthesis of Anilines

Anilines (2007)

  1. John F. Hartwig*,
  2. Shashank Shekhar,
  3. Qilong Shen,
  4. Fabiola Barrios-Landeros

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0391

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Hartwig, J. F., Shekhar, S., Shen, Q. and Barrios-Landeros, F. 2009. Synthesis of Anilines. Patai's Chemistry of Functional Groups. .

Author Information

  1. Yale University, Department of Chemistry, New Haven, Connecticut, USA

  1. *

    Current Address: A410 CLSL, Box 58-6, MC-712, Department of Chemistry, University of Illinois, 600 South Mathews Av., Urbana, Illinois 61801, USA. Fax: 217-244-8024; e-mail: jhartwig@uiuc.edu

Publication History

  1. Published Online: 15 DEC 2009
Table 1. Amination of 4-Chloroanisole with Morpholinea
EntryPd source (mol% Pd)Added phosphine (mol%)Conversionb(%)a TON
  1. a

    Conditions: 4-MeOC6H4Cl (1.0 mmol), morpholine (1.26 mmol), t-BuONa (1.39 mmol), toluene (3 mL), 110°C, 17 h.

  2. b

    Conversion to N-(4-methoxyphenyl)morpholine, average of two reactions, determined by GC (hexadecane standard); TON = turnover number.

1Pd(OAc)2 (0.1)P(Bu-t)2(o-biphenyl) (0.1)770
2Pd(OAc)2 (0.1)P(Bu-t)2(o-biphenyl) (0.2)26260
3Pd(OAc)2 (0.1)PCy2(o-biphenyl) (0.1)23.5235
4Pd(OAc)2 (0.1)PCy2(o-biphenyl) (0.2)62.5625
5Pd(OAc)2 (0.1)PCy3 (0.1)5.555
6Pd(OAc)2 (0.1)PCy3 (0.2)770
7Pd(OAc)2 (0.1)P(Bu-t)3 (0.1)110
8Pd(OAc)2 (0.1)P(Bu-t)3 (0.2)220
939 (0.10)P(Bu-t)3 (0.1)92920
1039 (0.05)P(Bu-t)3 (0.1)17340
1139 (0.05)PCy3 (0.1)3.570
1240 (0.50) 2550
1341 (0.50) 63126
1439 (0.05)PCy2(o-biphenyl) (0.1)41820
1539 (0.05)P(Bu-t)2(o-biphenyl) (0.1)22.5450