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Since directing groups are ligands, their effectiveness correlates with their affinities for metals. Common functional groups such as ketones usually are only weak ligands and thus often are poor DGs. This problem is solved by the use of a
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Sambiagio, C.; D. Schönbauer; R. Blieck; T. Dao-Huy; G. Pototschnig; P. Schaaf; T. Wiesinger; M. F. Zia; J. Wencel-Delord; T. Besset; B. U. W. Maes; M. Schnürch (2018).
300:
301:"Transient imines as 'next generation' directing groups for the catalytic functionalisation of C–H bonds in a single operation"
231:"Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics"
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condensation. Subsequent to serving their role as DGs, the imine can hydrolyze, regenerating the ketone and amine.
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183:"A Comprehensive Overview of Directing Groups Applied in Metal-Catalysed C–H functionalisation chemistry"
147:. Transient DGs reversibly convert weak DGs (e.g., ketones) into strong DG's (e.g., imines) via a
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He, Jian; Wasa, Masayuki; Chan, Kelvin S. L.; Shao, Qian; Yu, Jin-Quan (2017).
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Molecular substituent that facilitates reactions by interacting with a reagent
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Activation of a C–H bond via transient directing group provided by an
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252:"Palladium-Catalyzed Transformations of Alkyl C–H Bonds"
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299:St John-Campbell, S.; J. A. Bull (2018).
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113:, a reaction is typically applied to the
59:, where it is defined as a "coordinating
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7:
308:Organic & Biomolecular Chemistry
51:. The term is usually applied to
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75:." In a well known example, the
71:into the proximity of a certain
134:can serve as directing groups.
117:of substituted aromatic rings.
1:
268:10.1021/acs.chemrev.6b00622
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138:Transient directing groups
67:'), which directs a metal
229:Snieckus, Victor (1990).
145:transient directing group
125:Directed ortho metalation
111:directed ortho metalation
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127:
102:
101:. X = directing group.
47:by interacting with a
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320:10.1039/C8OB00926K
199:10.1039/C8CS00201K
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130:A wide variety of
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357:Organic reactions
314:(25): 4582–4595.
262:(13): 8754–8786.
193:(17): 6603–6743.
132:functional groups
87:is the DG in the
43:that facilitates
21:organic chemistry
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109:is related to
107:Murai reaction
99:Murai reaction
89:Murai reaction
63:(an 'internal
53:C–H activation
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240:(6): 879–933.
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85:acetophenone
57:hydrocarbons
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149:Schiff base
33:substituent
234:Chem. Rev.
166:References
115:lithiation
45:reactions
351:Category
338:29796566
286:28697604
217:30033454
73:C–H bond
69:catalyst
37:molecule
277:5516964
208:6113863
79:group (
49:reagent
31:) is a
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77:ketone
65:ligand
61:moiety
304:(PDF)
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282:PMID
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105:The
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324:hdl
316:doi
272:PMC
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