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Tsuji–Trost Reaction

Barry Trost

Barry Trost 1)

Barry M. Trost (born June 13, 1941 in Philadelphia) is an American chemist, Tamaki Professor of Humanities and Sciences at Stanford University.

He studied at the University of Pennsylvania and obtained his B.A. in 1962. His Ph.D. thesis research on The Structure and Reactivity of Enolate Anions was conducted at the Massachusetts Institute of Technology. He was professor at the University of Wisconsin–Madison from 1965 until his appointment to Stanford University in 1987.

The Tsuji Trost reaction and the Trost ligand are named after him. He is prominent for advancing the concept of atom economy.2) 3)

Main Features

  • The Tsuji–Trost reaction (also called the Trost allylic alkylation or allylic alkylation) is a palladium-catalysed substitution reaction involving a substrate that contains a leaving group in an allylic position. The palladium catalyst first coordinates with the allyl group and then undergoes oxidative addition, forming the π-allyl complex. This complex can then be attacked by a nucleophile, resulting in the substituted product.4)
  • Byproduct:
  • Drawbacks :
  • Driving force:
  • Stereochemistry and stereospecificity )

Reaction Mechanism

Synthetic Application

Review Articles

Similar Reactions

2) Trost, Barry M. (1991). “Atom Economy: A Search for Synthetic Efficiency”. Science 254 (5037): 1471–1477. doi:10.1126/science.1962206.
3) Trost, Barry M. (1995). “Atom Economy - A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way”. Angewandte Chemie International Edition 34 (3): 259–281. doi:10.1002/anie.199502591
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named/reactions/tsuji_trost_reaction.txt · Last modified: 2014/12/08 21:29 (external edit)

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