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

Frady G. Adly; Ashraf Ghanem

doi:10.1016/j.tetlet.2016.01.010

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

Frady G. Adly
, Ashraf Ghanem

Research output: Contribution to journal › Article › peer-review

18 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 language	English
Pages (from-to)	852-857
Number of pages	6
Journal	Tetrahedron Letters
Volume	57
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2016.01.010
Publication status	Published - 24 Feb 2016

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@article{db25454ea59f4d5389742a5ce5cf941f,

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",

note = "Funding Information: The authors gratefully acknowledge the W.J. Weeden scholarships program at the University of Canberra, Australia, for the Ph.D. scholarship offered to Dr. Frady Gamal Adly Gouany. Special acknowledgment is also due to A/Prof. Simon Foster from the Environmental Science Department at the University of Canberra for his assistance in the ICP-MS analysis. The authors would like also to thank Strem Chemicals for licensing and commercializing our catalyst 47 Rh 2 ( S - tert PTTL) 4 † (patent PCT/AU2015/000557) worldwide. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd. All rights reserved. Copyright: Copyright 2016 Elsevier B.V., All rights reserved. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd. All rights reserved.",

year = "2016",

month = feb,

day = "24",

doi = "10.1016/j.tetlet.2016.01.010",

language = "English",

volume = "57",

pages = "852--857",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "8",

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TY - JOUR

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

AU - Adly, Frady G.

AU - Ghanem, Ashraf

N1 - Funding Information: The authors gratefully acknowledge the W.J. Weeden scholarships program at the University of Canberra, Australia, for the Ph.D. scholarship offered to Dr. Frady Gamal Adly Gouany. Special acknowledgment is also due to A/Prof. Simon Foster from the Environmental Science Department at the University of Canberra for his assistance in the ICP-MS analysis. The authors would like also to thank Strem Chemicals for licensing and commercializing our catalyst 47 Rh 2 ( S - tert PTTL) 4 † (patent PCT/AU2015/000557) worldwide. Publisher Copyright: © 2016 Elsevier Ltd. All rights reserved. Copyright: Copyright 2016 Elsevier B.V., All rights reserved. Publisher Copyright: © 2016 Elsevier Ltd. All rights reserved.

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 - https://www.scopus.com/pages/publications/84956591509

U2 - 10.1016/j.tetlet.2016.01.010

DO - 10.1016/j.tetlet.2016.01.010

M3 - Article

SN - 0040-4039

VL - 57

SP - 852

EP - 857

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

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

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