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Cycloisomerization of Olefins in Water
Author(s) -
Matos Jeishla L. M.,
Green Samantha A.,
Chun Yuge,
Dang Vuong Q.,
Dushin Russell G.,
Richardson Paul,
Chen Jason S.,
Piotrowski David W.,
Paegel Brian M.,
Shenvi Ryan A.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202003948
Subject(s) - cycloisomerization , chemistry , bioorthogonal chemistry , catalysis , reagent , aqueous solution , combinatorial chemistry , nucleobase , biomolecule , dilution , organic chemistry , click chemistry , dna , biochemistry , physics , thermodynamics
Preparative reactions that occur efficiently under dilute, buffered, aqueous conditions in the presence of biomolecules find application in ligation, peptide synthesis, and polynucleotide synthesis and sequencing. However, the identification of functional groups or reagents that are mutually reactive with one another, but unreactive with biopolymers and water, is challenging. Shown here are cobalt catalysts that react with alkenes under dilute, aqueous, buffered conditions and promote efficient cycloisomerization and formal Friedel–Crafts reactions. The constraining conditions of bioorthogonal chemistry are beneficial for reaction efficiency as superior conversion at low catalyst concentration is obtained and competent rates in dilute conditions are maintained. Efficiency at high dilution in the presence of buffer and nucleobases suggests that these reaction conditions may find broad application.