The Vespiary

The Hive => Serious Chemistry => Topic started by: Rhodium on October 18, 2003, 10:42:00 AM

Title: Hydroamination routes to Amphetamines & PEAs
Post by: Rhodium on October 18, 2003, 10:42:00 AM

Review: Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines

Advanced Synthesis & Catalysis, 344(8), 795-813 (2002) (https://www.thevespiary.org/rhodium/Rhodium/pdf/base-cat.hydroamination.review.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/base-cat.hydroamination.review.pdf)
DOI:

10.1002/1615-4169(200209)344:83.0.CO;2-Q (http://dx.doi.org/10.1002/1615%2D4169%28200209%29344%3A8%26lt%3B795%3A%3AAID%2DADSC795%26gt%3B3.0.CO%3B2%2DQ)

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A Base-Catalyzed Domino-Isomerization–Hydroamination Reaction – New Synthetic Route to Amphetamines
DOI:

10.1016/S0040-4020(00)00436-1 (http://dx.doi.org/10.1016/S0040%2D4020%2800%2900436%2D1)

Tetrahedron 56(29), 5157-5162 (2000) (https://www.thevespiary.org/rhodium/Rhodium/pdf/hydroamination.allylbenzene2amphetamines.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/hydroamination.allylbenzene2amphetamines.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000414904-file_zfa6.gif)

Post 271694 (https://www.thevespiary.org/talk/index.php?topic=7569.msg27169400#msg27169400)

(foxy2: "Re: here it is: direct amination of allylbenzene", Chemistry Discourse)

Post 465442 (https://www.thevespiary.org/talk/index.php?topic=7569.msg46544200#msg46544200)

(Rhodium: "Hydroamination Route to Amphetamines", Chemistry Discourse)

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Amphetamines and phenyl-2-propanones from 1-phenylpropyne and amines

None (https://www.thevespiary.org/rhodium/Rhodium/pdf/catalytic.hydroamination.alkynes.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/catalytic.hydroamination.alkynes.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000414904-file_sxuq.gif)

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Hydroamination of Cinnamylalcohol (http://www.unibas.ch/mdpi/ecsoc-3/a0025/a0025.htm)

(http://www.unibas.ch/mdpi/ecsoc-3/a0025/a0025.htm)

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000414904-file_apnu.gif)

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Photoinduced amination of styrenes to phtalimide-protected phenethylamines

Post 429395 (https://www.thevespiary.org/talk/index.php?topic=12426.msg42939500#msg42939500)

(Rhodium: "Photophtalimidation of styrenes to PEAs", Serious Chemistry)

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000414904-file_a49z.gif)

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An Ammonia Equivalent for the Dimethyltitanocene-Catalyzed Intermolecular Hydroamination of Alkynes

Post 434626 (https://www.thevespiary.org/talk/index.php?topic=12027.msg43462600#msg43462600)

(ChemisTris: "Dimethyltitanocene cat. hydroamination of alkynes", Novel Discourse)

Org. Lett. 2(13), 1935-1937 (2000) (https://www.thevespiary.org/rhodium/Rhodium/pdf/dimethyltitanocene-hydroamination.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/dimethyltitanocene-hydroamination.pdf)
DOI:

10.1021/ol006011e (http://dx.doi.org/10.1021/ol006011e)

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000414904-file_sxuq.gif)

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Synthesis of allylic amines through the palladium-catalyzed hydroamination of allenes

Tetrahedron Letters 36(22), 3857-3860 (1995) (https://www.thevespiary.org/rhodium/Rhodium/pdf/hydroamination.allenes.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/hydroamination.allenes.pdf)
DOI:

10.1016/0040-4039(95)00656-W (http://dx.doi.org/10.1016/0040%2D4039%2895%2900656%2DW)

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000414904-file_wya3.gif)

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Riken Review No. 42, pp 53-56 (2001) (https://www.thevespiary.org/rhodium/Rhodium/pdf/ruthenium.hydroamination.1-alkynes.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/ruthenium.hydroamination.1-alkynes.pdf)

Ruthenium complexes that efficiently catalyze hydration and hydroamination of 1-alkynes have been found. The hydration described here is the first example of anti-Markovnikov regioselectivity to produce aldehydes. A mechanism involving Ru(IV)-hydride-vinylidene intermediate is proposed. A highly practical catalytic hydroamination method has also been developed which was applied to synthesis of nitrogen containing heterocycles.