General Method of Synthesis for Naloxone, Naltrexone, Nalbuphone, and Nalbuphine by the Reaction of Grignard Reagents with an Oxazolidine Derived from Oxymorphone

2013 ◽  
Vol 355 (9) ◽  
pp. 1869-1873 ◽  
Author(s):  
Mary Ann A. Endoma-Arias ◽  
D. Phillip Cox ◽  
Tomas Hudlicky
Keyword(s):  
Grignard Reagents ◽  
General Method

A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents

Tetrahedron ◽  
2015 ◽  
Vol 71 (24) ◽  
pp. 4248-4254 ◽  
Author(s):  
Pei-Qiang Huang ◽  
Yu Wang ◽  
Kai-Jiong Xiao ◽  
Ying-Hong Huang
Keyword(s):  
Grignard Reagents ◽  
Direct Transformation ◽  
Tertiary Amides ◽  
General Method

New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents

2009 ◽  
Vol 74 (5) ◽  
pp. 1939-1951 ◽  
Author(s):  
Yohei Kiyotsuka ◽  
Yuji Katayama ◽  
Hukum P. Acharya ◽  
Tomonori Hyodo ◽  
Yuichi Kobayashi
Keyword(s):  
Grignard Reagents ◽  
Allylic Substitution ◽  
General Method

The Formation of Ketones by a Reaction Equivalent to R-+R′COCH2+→R′COCH2R

1990 ◽  
Vol 43 (1) ◽  
pp. 133 ◽  
Author(s):  
AR Katritzky ◽  
L Wrobel ◽  
GP Savage ◽  
M Deyrupdrewniak
Keyword(s):  
Grignard Reagents ◽  
Aryl Ketones ◽  
General Method

A general method has been developed for the overall transformation of α- bromo ketones to α-alkyl or α-aryl ketones , with benzotriazole being used as a synthetic auxiliary. α- Benzotriazolyl ketones , when converted into their phenylhydrazones, reacted smoothly with alkyl and aryl Grignard reagents, which displaced benzotriazolate, to give the corresponding α-alkyl or α-aryl hydrazones. In some cases, these hydrolysed directly to the α-alkyl or α-aryl ketones. In each case, the product was treated with 2,4-dinitrophenylhydrazine to isolate the target ketones as the corresponding 2,4-dinitrophenylhydrazones.

scholarly journals Synthesis of All-carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada CrossCoupling

2020 ◽  
Author(s):  
Jeremy Nugent ◽  
Bethany Shire ◽  
Dimitri F. J. Caputo ◽  
Helena D. Pickford ◽  
Frank Nightingale ◽  
...  
Keyword(s):  
Drug Design ◽  
Reaction Times ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Mild Conditions ◽  
Broad Scope ◽  
Wide Range ◽  
Harsh Conditions ◽  
General Method

1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p-substituted arenes and alkynes. Access to all-carbon disubstituted BCPs via cross coupling has to date been limited to use of the BCP as the organometallic component, which restricts scope due to the harsh conditions typically required for the synthesis of metallated BCPs. Here we report a general method to access 1,3-C-disubstituted BCPs from 1-iodo-bicyclo[1.1.1]pentanes (iodo-BCPs) by direct iron-catalyzed crosscoupling with aryl and heteroaryl Grignard reagents. This chemistry represents the first general use of iodoBCPs as electrophiles in cross-coupling, and of Kumada coupling of tertiary iodides in general. Benefiting from short reaction times, mild conditions, and broad scope of the coupling partners, it enables the synthesis of a wide range of 1,3-C-disubstituted BCPs including various drug analogues.

ChemInform Abstract: New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents.

ChemInform ◽  
2009 ◽  
Vol 40 (29) ◽  
Author(s):  
Yohei Kiyotsuka ◽  
Yuji Katayama ◽  
Hukum P. Acharya ◽  
Tomonori Hyodo ◽  
Yuichi Kobayashi
Keyword(s):  
Grignard Reagents ◽  
Allylic Substitution ◽  
General Method

scholarly journals Synthesis of All-carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada CrossCoupling

2020 ◽  
Author(s):  
Jeremy Nugent ◽  
Bethany Shire ◽  
Dimitri F. J. Caputo ◽  
Helena D. Pickford ◽  
Frank Nightingale ◽  
...  
Keyword(s):  
Drug Design ◽  
Reaction Times ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Mild Conditions ◽  
Broad Scope ◽  
Wide Range ◽  
Harsh Conditions ◽  
General Method

1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p-substituted arenes and alkynes. Access to all-carbon disubstituted BCPs via cross coupling has to date been limited to use of the BCP as the organometallic component, which restricts scope due to the harsh conditions typically required for the synthesis of metallated BCPs. Here we report a general method to access 1,3-C-disubstituted BCPs from 1-iodo-bicyclo[1.1.1]pentanes (iodo-BCPs) by direct iron-catalyzed crosscoupling with aryl and heteroaryl Grignard reagents. This chemistry represents the first general use of iodoBCPs as electrophiles in cross-coupling, and of Kumada coupling of tertiary iodides in general. Benefiting from short reaction times, mild conditions, and broad scope of the coupling partners, it enables the synthesis of a wide range of 1,3-C-disubstituted BCPs including various drug analogues.

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