Asymmetric α-C(sp3)−H allylic alkylation of primary alkylamines by synergistic Ir/ketone catalysis

Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (p K a  ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acid...

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Published inNature communications Vol. 15; no. 1; pp. 939 - 8
Main Authors Li, Jianyu, Gong, Sheng, Gao, Shaolun, Chen, Jianfeng, Chen, Wen-Wen, Zhao, Baoguo
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 31.01.2024
Nature Publishing Group
Nature Portfolio
Subjects
639/638/77/883
639/638/77/889
Acidity
Alkylamines
Alkylation
Amination
Amines
Asymmetry
Bonding
Carbonates
Catalysis
Catalysts
Humanities and Social Sciences
Iridium
Ketones
Ligands
multidisciplinary
Science
Science (multidisciplinary)
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Abstract Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (p K a  ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C−H bonds by up to 10 44 times. This makes the α-amino C−H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C−H alkylation of NH 2 -unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C−H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step. Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles but their α-C–H bonds are unreactive towards electrophiles due to their extremely low acidity. Combining 8-diazafluoren-9-one with an iridium catalyst, the authors demonstrate direct asymmetric α-C-H alkylation of unprotected primary alkyl amines with allylic carbonates.
AbstractList Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (p K a  ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C−H bonds by up to 10 44 times. This makes the α-amino C−H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C−H alkylation of NH 2 -unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C−H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.
Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C-H bonds are unreactive towards electrophiles due to their extremely low acidity (pK  ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C-H bonds by up to 10 times. This makes the α-amino C-H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C-H alkylation of NH -unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C-H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.
Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C-H bonds are unreactive towards electrophiles due to their extremely low acidity (pKa ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C-H bonds by up to 1044 times. This makes the α-amino C-H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C-H alkylation of NH2-unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C-H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C-H bonds are unreactive towards electrophiles due to their extremely low acidity (pKa ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C-H bonds by up to 1044 times. This makes the α-amino C-H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C-H alkylation of NH2-unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C-H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.
Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (p K a  ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C−H bonds by up to 10 44 times. This makes the α-amino C−H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C−H alkylation of NH 2 -unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C−H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step. Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles but their α-C–H bonds are unreactive towards electrophiles due to their extremely low acidity. Combining 8-diazafluoren-9-one with an iridium catalyst, the authors demonstrate direct asymmetric α-C-H alkylation of unprotected primary alkyl amines with allylic carbonates.
Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (pKa ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C−H bonds by up to 1044 times. This makes the α-amino C−H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C−H alkylation of NH2-unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C−H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles but their α-C–H bonds are unreactive towards electrophiles due to their extremely low acidity. Combining 8-diazafluoren-9-one with an iridium catalyst, the authors demonstrate direct asymmetric α-C-H alkylation of unprotected primary alkyl amines with allylic carbonates.
Abstract Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (pK a ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C−H bonds by up to 1044 times. This makes the α-amino C−H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C−H alkylation of NH2-unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C−H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.
ArticleNumber 939
Author Gong, Sheng
Chen, Wen-Wen
Zhao, Baoguo
Gao, Shaolun
Chen, Jianfeng
Li, Jianyu
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/38296941$$D View this record in MEDLINE/PubMed
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– name: Nature Publishing Group
– name: Nature Portfolio
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Snippet Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to...
Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C-H bonds are unreactive towards electrophiles due to...
Abstract Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards...
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SubjectTerms 639/638/77/883
639/638/77/889
Acidity
Alkylamines
Alkylation
Amination
Amines
Asymmetry
Bonding
Carbonates
Catalysis
Catalysts
Humanities and Social Sciences
Iridium
Ketones
Ligands
multidisciplinary
Science
Science (multidisciplinary)
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Title Asymmetric α-C(sp3)−H allylic alkylation of primary alkylamines by synergistic Ir/ketone catalysis
URI https://link.springer.com/article/10.1038/s41467-024-45131-3
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Volume 15
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