Intramolecular C-H amination with sulfonyl azides

Details Intramolecular C-H amination with sulfonyl azides Intramolecular C-H amination with sulfonyl azides

2011-06-07

2011-06-07

Habte, Kahsay T (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C540S145000

Reexamination Certificate

active

07956193

ABSTRACT:
Cobalt (II) complexes of porphyrins are effective catalysts for intramolecular nitrene insertion of C—H bonds with arylsulfonyl azides. The cobalt-catalyzed process can proceed efficiently under mild and neutral conditions in low catalyst loading without the need of other reagents or additives, generating nitrogen gas as the only byproduct. Using the simple tetraphenylporphyrin (TPP) as the ligand, the cobalt-catalyzed intramolecular amidation can be applied to primary, secondary, and tertiary C—H bonds and suitable for a broad range of arylsulfonyl azides, leading to the syntheses of various benzosultam derivatives in excellent yields

REFERENCES:
patent: 6353112 (2002-03-01), Baker et al.
patent: 6365612 (2002-04-01), Genin et al.
patent: 6458962 (2002-10-01), Mao et al.
patent: 6562850 (2003-05-01), Baker et al.
patent: 6951935 (2005-10-01), Zhang et al.
patent: 2005/0124596 (2005-06-01), Zhang et al.
patent: 2006/0030718 (2006-02-01), Zhang et al.
Abramovitch et al., J. Org. Chem., 1977, 2920-2926, 42 (17).
Dauban et al., Synlett 2003, 1571-1586, No. 11.
Elgazwy, Tetrahedron 2003, 7445-7463, 59.
Espino et al., J. Am. Chem. Soc. 2001, 6935-6936, 123 (28).
Espino et al., Modern Rhodium-Catalyzed Organic Reactions, 2005, 379-416, Wiley-VCH, Weinheim.
Hansch et al., J. Org. Chem., 1956, 265-270, 21 (3).
Headrick, Dissertation 2003, University of Tennessee, Knoxville.
Rapoport et al., J. Org. Chem. 1988, 2367-2371, 53.
Ruppel et al., Organic Letters 2007, 4889-4892, 9 (23).
Zaharevitz et al., Med. Chem. Res. 1999, 551-564, 9.
Abdel-Sattar et al., Tetrahedron, 59, 7445-7463, 2003.
Albone et al., J. Org. Chem., 63, 9569-9571, 1998.
Antunes et al., Chem. Commun, 405-406, 2001.
Brase et al., Angew Chem. Int. Ed., 44, 5188-5240, 2005.
Cenini, et al., Chem. Commun. 2265-2266, 2000.
Cenini et al., Coor. Chem. Rev., 250, 1234-1253, 2006.
Chanda et al., J. Org. Chem., 66, 30-34, 2001.
Chen et al., JACS, 126, 14718-14719, 2004.
Chen et al., J. Org. Chem., 69, 2431-2435, 2004.
Chen et al., Tetrahedron Ltrs., 46, 4965-4969, 2005.
Cui, Angew Chem. Int., 43, 4210-4112, 2004.
Davies et al., Angew, 44 3518-3520, 2005.
Davies, Angew Chem. Int. Ed., 45 6422-6425, 2006.
Dauban et al., JACS, 123, 7707-7708, 2001.
Espino et al., Angew Chem. Int. Ed., 40, 598-600, 2001.
Gao et al., Org. Ltrs., 7, 3191-3193, 2005.
Gao, et al., J. Org. Chem., 71, 6655-6658, 2006.
Guthikonda et al., Jacs, 124, 13672-13673, 2002.
Halfen, Current Org. Chem., 9, 657-669, 2005.
Han et al., Tetrahedron Ltrs., 47, 7225-7228, 2006.
Huang et al., J. Org. Chem., 68, 8179-8184, 2003.
Katsuki et al., Chem. Ltrs., 34, 1304-1309, 2005.
Kawabata et al., Chem. Asian J., 2, 248-256, 2007.
Koser et al., Topics Current Chem., 224, 137-172, 2003.
Lebel et al., JACS, 127, 14198-14199, 2005.
Lebel et al., Pure Appl. Chem., 78, 363-375, 2006.
Lebel et al., Org. Ltrs., 9, 639-642, 2007.
Lee et al., Organometallics, 22, 4905-4909, 2003.
Lee et al., Curr. Org. Chem., 11, 213-228, 2007.
Liang et al., Angew Chem. Int.Liang, Angew Chem. Int., 45, 4641-4644, 2006, 45, 4641-4644, 2006.
Liu, et al., Heterocycles, vol. 56, 693-709, 2002.
Muller et al., Chem. Rev., 103, 2905-2919, 2003.
Omura et al., Chem. Ltrs., 32, 354-355, 2003.
Omura et al., Chem. Comm., 2060-2061, 2004.
Piangiolino et al., Eur. J. Org. Chem., 743-750, (2007).
Ragaini et al., Chem. Eur. J., 9, 249, 2003.
Reddy et al., Org. Ltrs., 8, 5013-5016, 2006.
Scriven et al., Chem. Rev., 88, 297-368, 1988.
Simkhovich et al., Tetrahedron Ltrs., 42, 8089-8092, 2001.
Vyas et al., Org. Ltrs., 6, 1907-1910, 2004.
Yu et al., Organic Ltrs., 2, 2233-2236, 2000.

Affiliated with

Also associated with

Rating

Intramolecular C-H amination with sulfonyl azides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Intramolecular C-H amination with sulfonyl azides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intramolecular C-H amination with sulfonyl azides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2684873