Hydroamination: Difference between revisions – Wikipedia

In [[organic chemistry]], ”’hydroamination”’ is the [[Addition reaction|addition]] of an {{chem2|NsH}} bond of an [[amine]] across a [[Carbon–carbon bond|carbon-carbon multiple bond]] of an [[alkene]], [[alkyne]], [[diene]], or [[allene]].{{cite book |last1=Togni |first1= Antionio |last2=Grützmacher |first2=Hansjörg |title=Catalytic heterofunctionalization: from hydroanimation to hydrozirconation |year=2001 |publisher=Wiley-VCH |location=Weinheim |isbn=978-3527302345 |edition=1. |doi=10.1002/3527600159}} In the ideal case, hydroamination is [[atom economy|atom economical]] and [[green chemistry|green]].{{cite book |last1=Beller |first1=M. |last2=Bolm |first2=C.|title=Transition metals for organic synthesis : building blocks and fine chemicals |year=2004 |publisher=Wiley-VCH |location=Weinheim |isbn=9783527306138| edition=2nd |doi=10.1002/9783527619405}} Amines are common in fine-chemical, pharmaceutical, and agricultural industries.{{cite book | last1 = Reznichenko | first1 = A. L. | last2 = Hultszch | first2 = K. C. | year = 2015 | title = Hydroamination of Alkenes |journal=[[Org. React.]] | volume = 88 | page = 1 | doi=10.1002/0471264180.or088.01| isbn = 978-0471264187}}{{cite journal | first = Kai C. | last = Hultzsch | title =Catalytic asymmetric hydroamination of non-activated olefins | type = Review | journal = [[Org. Biomol. Chem.]] | year = 2005 | volume = 3 | pages = 1819–1824 | doi = 10.1039/b418521h | pmid = 15889160 | issue = 10}}{{cite journal | author = Hartwig, J. F. | author-link = John F. Hartwig | url = http://www.iupac.org/publications/pac/2004/pdf/7603×0507.pdf | title = Development of catalysts for the hydroamination of olefins | journal = [[Pure Appl. Chem.]] | year = 2004 | volume = 76 | pages = 507–516 | doi = 10.1351/pac200476030507 | issue = 3}}{{cite journal |author1=Pohlki, F. |author2=Doye, S. |title=The catalytic hydroamination of alkynes |journal=[[Chem. Soc. Rev.]] |year=2003 |volume=32 |pages=104–114 |doi=10.1039/b200386b |pmid=12683107}} Hydroamination can be used [[intramolecular reaction|intramolecularly]] to create [[heterocyclic compounds|heterocycles]] or intermolecularly with a separate amine and [[unsaturated compound]]. The development of [[catalyst]]s for hydroamination remains an active area, especially for alkenes. Although practical hydroamination reactions can be effected for dienes and electrophilic alkenes, the term hydroamination often implies reactions metal-catalyzed processes.

In [[organic chemistry]], ”’hydroamination”’ is the [[Addition reaction|addition]] of an {{chem2|NsH}} bond of an [[amine]] across a [[Carbon–carbon bond|carbon-carbon multiple bond]] of an [[alkene]], [[alkyne]], [[diene]], or [[allene]].{{cite book |last1=Togni |first1= Antionio |last2=Grützmacher |first2=Hansjörg |title=Catalytic heterofunctionalization: from hydroanimation to hydrozirconation |year=2001 |publisher=Wiley-VCH |location=Weinheim |isbn=978-3527302345 |edition=1. |doi=10.1002/3527600159}} In the ideal case, hydroamination is [[atom economy|atom economical]] and [[green chemistry|green]].{{cite book |last1=Beller |first1=M. |last2=Bolm |first2=C.|title=Transition metals for organic synthesis : building blocks and fine chemicals |year=2004 |publisher=Wiley-VCH |location=Weinheim |isbn=9783527306138| edition=2nd |doi=10.1002/9783527619405}} Amines are common in fine-chemical, pharmaceutical, and agricultural industries.{{cite book | last1 = Reznichenko | first1 = A. L. | last2 = Hultszch | first2 = K. C. | year = 2015 | title = Hydroamination of Alkenes |journal=[[Org. React.]] | volume = 88 | page = 1 | doi=10.1002/0471264180.or088.01| isbn = 978-0471264187}}{{cite journal | first = Kai C. | last = Hultzsch | title =Catalytic asymmetric hydroamination of non-activated olefins | type = Review | journal = [[Org. Biomol. Chem.]] | year = 2005 | volume = 3 | pages = 1819–1824 | doi = 10.1039/b418521h | pmid = 15889160 | issue = 10}}{{cite journal | author = Hartwig, J. F. | author-link = John F. Hartwig | url = http://www.iupac.org/publications/pac/2004/pdf/7603×0507.pdf | title = Development of catalysts for the hydroamination of olefins | journal = [[Pure Appl. Chem.]] | year = 2004 | volume = 76 | pages = 507–516 | doi = 10.1351/pac200476030507 | issue = 3}}{{cite journal |author1=Pohlki, F. |author2=Doye, S. |title=The catalytic hydroamination of alkynes |journal=[[Chem. Soc. Rev.]] |year=2003 |volume=32 |pages=104–114 |doi=10.1039/b200386b |pmid=12683107}} Hydroamination can be used [[intramolecular reaction|intramolecularly]] to create [[heterocyclic compounds|heterocycles]] or intermolecularly with a separate amine and [[unsaturated compound]]. The development of [[catalyst]]s for hydroamination remains an active area, especially for alkenes. Although practical hydroamination reactions can be effected for dienes and electrophilic alkenes, the term…