Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format

Frady G. Adly, Ashraf Ghanem

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44%) and excellent diastereoselectivity (>20:1 E:Z dr).
Original languageEnglish
Pages (from-to)852-857
Number of pages6
JournalTetrahedron Letters
Volume57
Issue number8
DOIs
Publication statusPublished - 24 Feb 2016

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Miniaturization
Catalyst supports
Leaching
Polymers
Catalysts
pyridine
cyclopropane

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title = "Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format",
abstract = "Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44{\%}) and excellent diastereoselectivity (>20:1 E:Z dr).",
keywords = "Cyclopropanation, Dirhodium, Metal-carbenoids, Microreactor, Rh2(S-PTTL)4, Rh2(S-tertPTTL)4, Rh-2(S-PTTL)(4), Rh-2(S-(PTTL)-P-tert)(4)",
author = "Adly, {Frady G.} and Ashraf Ghanem",
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Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format. / Adly, Frady G.; Ghanem, Ashraf.

In: Tetrahedron Letters, Vol. 57, No. 8, 24.02.2016, p. 852-857.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format

AU - Adly, Frady G.

AU - Ghanem, Ashraf

PY - 2016/2/24

Y1 - 2016/2/24

N2 - Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44%) and excellent diastereoselectivity (>20:1 E:Z dr).

AB - Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44%) and excellent diastereoselectivity (>20:1 E:Z dr).

KW - Cyclopropanation

KW - Dirhodium

KW - Metal-carbenoids

KW - Microreactor

KW - Rh2(S-PTTL)4

KW - Rh2(S-tertPTTL)4

KW - Rh-2(S-PTTL)(4)

KW - Rh-2(S-(PTTL)-P-tert)(4)

UR - http://www.mendeley.com/research/polymer-monolithsupported-dirhodiumiicatalyzed-continuous-flow-cyclopropanation-capillary-format

U2 - 10.1016/j.tetlet.2016.01.010

DO - 10.1016/j.tetlet.2016.01.010

M3 - Article

VL - 57

SP - 852

EP - 857

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -