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Synthesis 2015; 47(04): 439-459
DOI: 10.1055/s-0034-1379890
DOI: 10.1055/s-0034-1379890
review
Transition-Metal-Catalyzed Direct C–H Functionalization under External-Oxidant-Free Conditions
Further Information
Publication History
Received: 26 September 2014
Accepted after revision: 14 November 2014
Publication Date:
21 January 2015 (online)
Abstract
The use of an ‘internal’ oxidant contained within a directing group has emerged as a practical strategy in metal-catalyzed direct C–H activations in recent years, owing to its being highly sustainable. This review presents the rapid advances of this novel strategy through analyzing and comparing the different types of internal oxidant in transition-metal-catalyzed C–H activation reactions.
1 Introduction
2 The N–O Bond as Internal Oxidant
2.1 The O-Linked Moiety as Leaving Group
2.1.1 N-Oxide
2.1.2 N-Acyloxy
2.1.3 Oxime
2.1.4 N-Methoxy or N-Hydroxy
2.1.5 N-Pivaloyloxy or O-tert-Butyloxycarbonyloxy
2.1.6 Miscellaneous
2.2 The N-Linked Moiety as Leaving Group
3 The N–N Bond as Internal Oxidant
4 The N–S Bond as Internal Oxidant
5 The S–Cl Bond as Internal Oxidant
5 The Si–H Bond as Internal Oxidant
6 Conclusion
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For reviews related with internal oxidant, see:
For similar reactions, see:
The transformation was also acheived by ruthenium catalysis; for related reports, see:
For a similar transformation, see:
For similar transformations, see:
With respect to organic alcohols further C–H functionalization that involve C–H/C–O cleavages, see:
For a similar example of C–H functionalizations through S–Cl bond cleavage, see:
For a similar transformation, see:
For a similar transformation, see: