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Tuning the Porphyrin Building Block in Self-Assembled Cages for Branched-Selective Hydroformylation of Propene.


ABSTRACT: Unprecedented regioselectivity to the branched aldehyde product in the hydroformylation of propene was attained on embedding a rhodium complex in supramolecular assembly L2, formed by coordination-driven self-assembly of tris(meta-pyridyl)phosphine and zinc(II) porpholactone. The design of cage L2 is based on the ligand-template approach, in which the ligand acts as a template for cage formation. Previously, first-generation cage L1, in which zinc(II) porphyrin units were utilized instead of porpholactones, was reported. Binding studies demonstrate that the association constant for the formation of second-generation cage L2 is nearly an order of magnitude higher than that of L1. This strengthened binding allows cage L2 to remain intact in polar and industrially relevant solvents. As a consequence, the unprecedented regioselectivity for branched aldehyde products can be maintained in polar and coordinating solvents by using the second-generation assembly.

SUBMITTER: Wang X 

PROVIDER: S-EPMC5697640 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Tuning the Porphyrin Building Block in Self-Assembled Cages for Branched-Selective Hydroformylation of Propene.

Wang Xiaowu X   Nurttila Sandra S SS   Dzik Wojciech I WI   Becker René R   Rodgers Jody J   Reek Joost N H JNH  

Chemistry (Weinheim an der Bergstrasse, Germany) 20170817 59


Unprecedented regioselectivity to the branched aldehyde product in the hydroformylation of propene was attained on embedding a rhodium complex in supramolecular assembly L2, formed by coordination-driven self-assembly of tris(meta-pyridyl)phosphine and zinc(II) porpholactone. The design of cage L2 is based on the ligand-template approach, in which the ligand acts as a template for cage formation. Previously, first-generation cage L1, in which zinc(II) porphyrin units were utilized instead of por  ...[more]

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