Literature DB >> 10814403

Selective hydrogenation of benzophenones to benzhydrols. Asymmetric synthesis of unsymmetrical diarylmethanols

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Abstract

[reaction: see text] trans-RuCl2[P(C6H4-4-CH3)3]2(NH2CH2CH2NH2) acts as a highly effective precatalyst for the hydrogenation of a variety of benzophenone derivatives to benzhydrols that proceeds smoothly at 8 atm and 23-35 degrees C in 2-propanol containing t-C4H9OK with a substrate/catalyst ratio of 2000-20000. Use of a BINAP/chiral diamine Ru complex effects asymmetric hydrogenation of various ortho-substituted benzophenones and benzoylferrocene to chiral diarylmethanols with consistently high ee.

Entities:  

Year:  2000        PMID: 10814403     DOI: 10.1021/ol9904139

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  13 in total

1.  Toward efficient asymmetric hydrogenation: architectural and functional engineering of chiral molecular catalysts.

Authors:  Ryoji Noyori; Masato Kitamura; Takeshi Ohkuma
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-19       Impact factor: 11.205

2.  A remarkably effective copper(II)-dipyridylphosphine catalyst system for the asymmetric hydrosilylation of ketones in air.

Authors:  Jing Wu; Jian-Xin Ji; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2005-02-22       Impact factor: 11.205

3.  Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Authors:  Taegyo Lee; Tyler W Wilson; Robert Berg; Per Ryberg; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-05-20       Impact factor: 15.419

4.  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups.

Authors:  Julien Rolland; Xacobe C Cambeiro; Carles Rodríguez-Escrich; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2009-10-15       Impact factor: 2.883

5.  Practical catalytic asymmetric synthesis of diaryl-, aryl heteroaryl-, and diheteroarylmethanols.

Authors:  Luca Salvi; Jeung Gon Kim; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

Review 6.  Asymmetric hydrogenation of ketones: tactics to achieve high reactivity, enantioselectivity, and wide scope.

Authors:  Takeshi Ohkuma
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493

7.  (2-Methyl-phen-yl)(phen-yl)methanol.

Authors:  B P Siddaraju; H S Yathirajan; B Narayana; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-31

8.  Methyl 2,2-diphenyl-2-(prop-2-yn-1-yl-oxy)acetate.

Authors:  H P Sumathi; Ulrich Flörke; H S Yathirajan; A S Dayananda; A R Ramesha
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-29

9.  2-(2-Benzyl-phen-yl)propan-2-ol.

Authors:  Richard Betz; Thomas Gerber; Eric Hosten; B P Siddaraju; Hemmige S Yathirajan; A R Ramesha
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-12

10.  2-[(2-Chloro-phen-yl)(hy-droxy)meth-yl]phenol.

Authors:  G Prakasha; Jerry P Jasinski; Jared S Brown; H S Yathirajan; D K Ravishankara
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-07-13
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