O-Protected NH-free hydroxylamines: emerging electrophilic aminating reagents for organic synthesis

In this highlight, O-protected NH-free hydroxylamine derivatives have been evaluated in the construction of nitrogen-enriched compounds, such as primary amines, amides, and N-heterocycles, with high regio-, chemo- and stereoselectivity in the unprotected form, showcasing the late-stage functionaliza...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 99; pp. 13495 - 1355
Main Authors Jinan, Dilsha, Mondal, Pinku Prasad, Nair, Anagha Veluthanath, Sahoo, Basudev
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 14.12.2021
Subjects
Amides
Amines
Natural products
Nitrogen
Reagents
Stereoselectivity
Transition metals
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Summary:In this highlight, O-protected NH-free hydroxylamine derivatives have been evaluated in the construction of nitrogen-enriched compounds, such as primary amines, amides, and N-heterocycles, with high regio-, chemo- and stereoselectivity in the unprotected form, showcasing the late-stage functionalization of natural products, drugs and functional molecules by biocatalysis, organocatalysis, and transition metal catalysis. The reactivity dichotomy among these N-O reagents has been explored based on SET and metal-nitrenoids. O-Protected NH-free hydroxylamines have emerged as electrophilic aminating reagents for constructing nitrogen-enriched compounds with high regio-, and stereoselectivity in the unprotected form, through biocatalysis, organo-, and metal catalysis.
Bibliography:Pinku Prasad Mondal completed his BSc in chemistry from Midnapore College in 2018, and MSc in Chemistry from the Indian Institute of Technology (IIT-ISM) Dhanbad (India) in 2020. In January 2021, he joined the group of Dr Basudev Sahoo at IISER Thiruvananthapuram for PhD studies, where his research is focused on sustainable organic synthesis based on transition-metal catalysis.
Dilsha Jinan completed her BSc in chemistry from DGMMES Mampad college (Calicut University) in 2017, and MSc in Organic Chemistry from National Institute of Technology (NIT) Warangal (India) in 2019. In August 2020, she joined the group of Dr Basudev Sahoo at IISER Thiruvananthapuram for her PhD, where she is working on organic synthesis for developing catalytic methods for amine synthesis.
Anagha Veluthanath Nair joined the Indian Institute of Science Education and Research (IISER) Thiruvananthapuram for her BS-MS Dual degree (chemistry major) in 2018. In May 2021, she joined the group of Dr Basudev Sahoo at IISER Thiruvananthapuram for her research internship, focusing on organic synthesis based on transition metal catalysis.
Basudev Sahoo obtained his PhD from WWU Muenster under the supervision of Prof. Frank Glorius. Afterwards he worked as a postdoctoral researcher in the laboratories of Prof. Matthias Beller at LIKAT, Rostock and in the research group of Prof. Ruben Martin as a Marie Curie postdoctoral fellow at ICIQ, Tarragona. Since March 2020, he is holding a position of Assistant Professor at IISER Thiruvananthapuram. His current research is focused on sustainable organic synthesis, including visible light photocatalysis, transition-metal catalysis and metal-free coupling chemistry.
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ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc05282a