2017
DOI: 10.1021/acs.orglett.7b02395
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Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis

Abstract: Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-… Show more

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Cited by 67 publications
(34 citation statements)
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“…With the aim of avoiding organotin reagents, an equivalent protocol to SnAP was developed by the Bode group, called silicon amine protocol (SLAP), which uses silicon instead of tin reagents. [58] For this transformation the organic photoredox catalyst 2,4,6-triphenylpyrylium tetrafluoroborate and blue light are necessary (Scheme 8). Besides avoiding toxic tin byproducts, an additional advantage of the SLAP protocol is its amenability to be performed under flow conditions.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…With the aim of avoiding organotin reagents, an equivalent protocol to SnAP was developed by the Bode group, called silicon amine protocol (SLAP), which uses silicon instead of tin reagents. [58] For this transformation the organic photoredox catalyst 2,4,6-triphenylpyrylium tetrafluoroborate and blue light are necessary (Scheme 8). Besides avoiding toxic tin byproducts, an additional advantage of the SLAP protocol is its amenability to be performed under flow conditions.…”
Section: Methodsmentioning
confidence: 99%
“…Reagents and conditions: a) 4 Å MS, MeCN, rt; b) 2,4,6-triphenylpyrylium tetrafluoroborate (5 mol %), TMSOTf (1.30 equiv), MeCN/HFIP 10 : 1, blue light (overall yield: 55-94 %). [58] (TMSOTf: trimethylsilyl trifluoromethanesulfonate). [59] (THF: tetrahydrofuran, TFA: trifluoroacetic acid, DMF: dimethylformamide).…”
Section: Methodsmentioning
confidence: 99%
“…The morpholine-containing building blocks exhibit wide range of biological activities such as antibacterial, antifungal, antiviral, anti-inflammatory, anticancer, and antioxidant activity. [24][25][26] Initially, we used phenyl acetylene (1a), N,N′-diisopropylcarbodiimide (2a), and methyl oxirane (3a) as the starting materials, CuI as precatalyst, and t BuOLi as base in NMP at 60°C. The desired product 4a was obtained only in 24% ( 4 ]PF 6 afforded a better yield (entry 4).…”
Section: Introductionmentioning
confidence: 99%
“…A SET oxidation‐desilylation of benzyltrimethysilanes involving visible‐light excited chiral iminium ions, 9‐mesityl‐10‐methylacridinium perchlorate salt or graphitic carbon nitride as a catalytic and strong photooxidant, allowed the formation of benzylic radicals which can be trapped by ground‐state iminium ions or Michael ‐type acceptors respectively. In the same vein, α ‐alkoxymethyl radicals were successfully generated from the corresponding α ‐silyl ethers by photocatalyzed oxidation, as well as acyl radicals from acyl silanes . But interestingly, what about the reactivity of hypercoordinated silicon derivatives under oxidative conditions?…”
Section: Introductionmentioning
confidence: 99%