O-Acyl oximes: versatile building blocks for N-heterocycle formation in recent transition metal catalysis
O -Acyl oximes are versatile building blocks being widely applied in organic synthesis, especially for N-heterocycle construction under transition metal catalysis. In the last decade, aza-Heck cyclization using oximes has been progressing in the preparation of functionalized pyrrolines, and instead...
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| Published in | Organic & biomolecular chemistry Vol. 14; no. 5; pp. 1519 - 153 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
England
07.02.2016
|
| Online Access | Get full text |
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| Summary: | O
-Acyl oximes are versatile building blocks being widely applied in organic synthesis, especially for N-heterocycle construction under transition metal catalysis. In the last decade, aza-Heck cyclization using oximes has been progressing in the preparation of functionalized pyrrolines, and instead of Pd catalysis, copper-based catalytic systems were found to work well in some cases.
O
-Acyl oximes as oxidizing directing groups have attracted intensive attention in transition metal-mediated C-H activation reactions, which avoid the use of external oxidants to feature advantages including mild reaction conditions, higher levels of reactivities, chemo-selectivities,
etc
. Moreover, catalytic α C(sp
3
)-H functionalization of
O
-acyl oximes and subsequent annulations provide a lot of opportunities for novel N-heterocycle synthesis. These transformations feature certain advantages: diversified and poly-functionalized products, mild and easy handling conditions, oximes serving as an internal oxidant to avoid the use of external oxidants, and so forth.
This review is dedicated to showcase and discuss recent progress on N-heterocycle formation by transition-metal catalyzed annulation from
O
-acyl oximes. |
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| Bibliography: | Jinhui Cai was born in Hunan Province, China in 1992. He received his B.S. degree from Xiangtan University (2014, Jun). Then he started his postgraduation study for his master's degree in Xiangtan University under the cooperative supervision of Prof. Guo-Jun Deng and Dr Huawen Huang. His current research is mainly focused on catalytic organic synthesis. Huawen Huang was born in Hunan Province, China in 1987. He received his B.S. degree from Northwest University (2009), and Ph.D. degree from the South China University of Technology (SCUT) under the supervision of Professor Huanfeng Jiang (2014, Jun). Then he joined the Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education at College of Chemistry, Xiangtan University. His current research is focused on a novel oxidative pattern and process for catalytic organic synthesis. Guo-Jun Deng received his B.S. degree from Xiangtan University and completed his Ph.D. degree in 2004 in chemistry from the Institute of Chemistry, Chinese Academy of Sciences with Prof. Qinhua Fan. Then he conducted post-doctoral studies with Prof. Lukas J. Goossen at Max Planck Institute, with Prof. E. Schoffers at Western Michigan University and with Prof. Chao-Jun Li at Tulane University and McGill University. In 2009, he joined the College of Chemistry at Xiangtan University as a full professor. His research interests lie in the development of environmentally benign methodologies for C-C and C-hetero bond formation. ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-3 content type line 23 ObjectType-Review-1 |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/c5ob02417j |