Carbon-heteroatom bond formation catalysed by organometallic complexes.
At one time the synthetic chemist's last resort, reactions catalysed by transition metals are now the preferred method for synthesizing many types of organic molecule. A recent success in this type of catalysis is the discovery of reactions that form bonds between carbon and heteroatoms (such as nitrogen, oxygen, sulphur, silicon and boron) via complexes of transition metals with amides, alkoxides, thiolates, silyl groups or boryl groups. The development of these catalytic processes has been supported by the discovery of new elementary reactions that occur at metal-heteroatom bonds and by the identification of factors that control these reactions. Together, these findings have led to new synthetic processes that are in daily use and have formed a foundation for the development of processes that are likely to be central to synthetic chemistry in the future.
Hartwig
John F
JF
Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. jhartwig@uiuc.edu
D000475:Alkenes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*
D000475:Alkenes; D008670:Metals; D009942:Organometallic Compounds; D002244:Carbon; D006859:Hydrogen
Science. 2000 Mar 17;287(5460):1995-7
10720320
Angew Chem Int Ed Engl. 2001 Feb 2;40(3):534-540
11180362
J Am Chem Soc. 2001 Mar 21;123(11):2576-87
11456927
J Org Chem. 1997 Oct 17;62(21):7082-7083
11671803
J Org Chem. 1999 Jul 23;64(15):5575-5580
11674624
Chem Rev. 2000 Apr 12;100(4):1169-204
11749263
Chem Rev. 2000 Jul 12;100(7):2537-74
11749295
Acc Chem Res. 2002 Jan;35(1):44-56
11790088
Chem Rev. 1997 Dec 18;97(8):2879-2932
11851481
Nature. 2002 May 30;417(6888):507-14
12037558
J Org Chem. 2002 Aug 9;67(16):5553-66
12153253
Angew Chem Int Ed Engl. 2002 Dec 16;41(24):4746-8
12481346
Angew Chem Int Ed Engl. 2003 Jun 23;42(24):2708-10
12820251
Chem Commun (Camb). 2004 Jan 7;(1):38-9
14737321
J Am Chem Soc. 2004 Mar 17;126(10):3036-7
15012118
J Am Chem Soc. 2004 Aug 11;126(31):9542-3
15291549
Acc Chem Res. 2004 Sep;37(9):673-86
15379583
Angew Chem Int Ed Engl. 2005 Feb 18;44(9):1371-5
15666413
Science. 2005 Feb 18;307(5712):1080-2
15718464
J Am Chem Soc. 2005 Mar 2;127(8):2538-52
15725009
Angew Chem Int Ed Engl. 2005 Mar 29;44(14):2112-5
15729724
Org Lett. 2005 Apr 28;7(9):1737-9
15844894
J Am Chem Soc. 2005 Aug 31;127(34):12066-73
16117547
J Am Chem Soc. 2005 Sep 21;127(37):12790-1
16159259
J Am Chem Soc. 2005 Oct 12;127(40):13754-5
16201772
J Am Chem Soc. 2005 Dec 21;127(50):17778-88
16351107
J Am Chem Soc. 2006 Mar 8;128(9):2893-901
16506768
J Inorg Biochem. 2006 Apr;100(4):434-47
16516297
Science. 2006 Apr 14;312(5771):257-61
16614220
J Am Chem Soc. 2006 Jun 7;128(22):7134-5
16734446
J Am Chem Soc. 2006 Jul 19;128(28):9044-5
16834372
J Am Chem Soc. 2006 Aug 2;128(30):9642-3
16866513
J Am Chem Soc. 2006 Aug 9;128(31):10028-9
16881628
Angew Chem Int Ed Engl. 2007;46(3):354-8
17029322
Inorg Chem. 2007 Mar 19;46(6):1936-47
17348724
J Am Chem Soc. 2007 May 16;129(19):6328-35
17439217
J Am Chem Soc. 2007 Aug 22;129(33):10102-3
17655312
J Am Chem Soc. 2007 Aug 29;129(34):10382-93
17672451
Angew Chem Int Ed Engl. 2007;46(40):7674-7
17786903
Angew Chem Int Ed Engl. 2007;46(46):8862-5
17943927
Nature. 2007 Nov 8;450(7167):243-51
17994091
J Am Chem Soc. 2007 Dec 12;129(49):15142-3
18004863
Angew Chem Int Ed Engl. 2008;47(3):586-8
18058877
Chem Commun (Camb). 2008 Mar 28;(12):1422-4
18338043
European J Org Chem. 2007 Feb;2007(4):571-582
20577649
Angew Chem Int Ed Engl. 1998 Sep 4;37(16):2180-2192
29711451
Science. 1998 Apr 24;280(5363):560-4
9554841