919119-69-0

Basic information

• Product Name: 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE
• Synonyms: 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE
• CAS NO: 919119-69-0
• Molecular Formula: C17H22BNO2
• Molecular Weight: 0
• Mol File: 919119-69-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE(919119-69-0)
• EPA Substance Registry System: 7-(4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROCYCLO-PENT[B]INDOLE(919119-69-0)

Safety Data

• Hazardous Substances Data: 919119-69-0(Hazardous Substances Data)

Upstream product

• 2047-91-8 2,3-dihydro-1H-cyclopentindole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.

Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles

Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright

Microwave-accelerated iridium-catalyzed borylation of aromatic C-H bonds

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Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation

Ir-catalyzed borylation of 2-substituted indoles selectively yields 7-borylated products in good yields. N-Protection, required for previous functionalizations of 2-substituted indoles, is unnecessary. Copyright