IP Library Granted Patent US 8,188,302
Granted Patent B2
US 8,188,302 · App. 12/251,062 · Granted May 29, 2012

Hydroamination of alkenes

Assignee: The Board of Trustees of the University of Illinois
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Quick Facts
Patent No.
US 8,188,302
App. No.
12/251,062
Granted
May 29, 2012
Kind
B2
Abstract

A method includes reacting an amino group, a composition including rhodium and an organic ligand, and a substrate having structural formula (I) in a reaction mixture. R 1 is an organic group including a sp 3 carbon atom bonded to C A . R 2 is selected from the group consisting of hydrogen, methyl, and an organic group including a sp 3 carbon atom bonded to C A . R 3 and R 4 independently are selected from the group consisting of hydrogen, methyl, and an organic group including a sp 3 carbon atom bonded to C B . The method further includes forming a hydroaminated product in the reaction mixture.

Claims (12)

1. A composition, comprising:

a rhodium complex comprising

a central rhodium atom,

at least one ancillary ligand selected from the group consisting of cyclooctadiene, cyclooctene, acetonitrile and acetone, and

a counterion selected from the group consisting of Cl − , Br − , AcO − , TfO − , CF 3 CO 2 − , BF 4 − , ClO 4 − , ReO 4 − , AsF 6 − and SbF 6 − , and

an organic ligand, selected from the group consisting of 4,5-(bis[bis-diethylamido]-phosphonito-9,9-dimethylxanthene and 2-dicyclohexyl-phosphino-2′-(N,N-dimethylamino)-biphenyl.

2. The composition of claim 1 , where the mole ratio of ligand to rhodium is from 0.8 to 2.

3. The composition of claim 1 , where the mole ratio of ligand to rhodium is from 0.9 to 1.5.

4. The composition of claim 1 , where the mole ratio of ligand to rhodium is from 1 to 1.2.

5. A catalyst, comprising:

a rhodium complex selected from the group consisting of [Rh(COD) 2 ]BR 4 , [Rh(MeCN) 2 (COD)]BF 4 , [Rh(COE) 2 Cl] 2 and [Rh(COD)Cl] 2 and

an organic ligand, selected from the group consisting of 4,5-(bis[bis-diethylamido]-phosphonito-9,9-dimethylxanthene and 2-dicyclohexyl-phosphino-2′-(N,N-dimethylamino)-biphenyl.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2012
From: TAKEMIYA, AKIHIRO; LIU, ZHIJIAN; HARTWIG, JOHN E.
To: BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS
Reel/Frame 027928/0451 →
CONFIRMATORY LICENSE Recorded Dec 16, 2010
From: UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 025498/0832 →
CONFIRMATORY LICENSE Recorded Apr 19, 2010
From: UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 024249/0914 →
Continuity (2)
Provisional Application 60979652 · Oct 12, 2007
Related Publication 20090156824A1 · Jun 18, 2009