Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation

Abstract

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

Synthesis, Structure, and Reactivity of Anionic sp2–sp3 Diboron Compounds: Readily Accessible Boryl Nucleophiles

“…Similar systems were recently studied by Blanchet et al 23f. g and Xue et al 23h. Because this reaction takes place in the presence of an alkoxide formed in situ from the reaction of t BuONO with the aryl amine, the reaction of an activated sp 2 –sp 3 derivative of 1 with the very electrophilic diazonium salt has to be considered as a possible reaction pathway (see below) for the synthesis of useful aryl boronates 22–24…”

Base‐Free Palladium‐Catalyzed Borylation of Aryl Chlorides with Diborons

“…[1] Thus, the developmento fnew methods to synthesize arylboronate esters under mild reaction conditions is important in moderno rganic chemistry. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Accordingly,transition-metal-catalyzed borylation reactions of aryl halides with diborons have emerged as efficient and reliable methods. [2-4, 5b, 6b, 9f,g,11] In these catalytic borylation reactions, the presenceo fabase is essential to activate the diboron for smooth boryl transfer.I tw ould be desirable to develop basefree conditions to achieve the synthesis of arylboronates bearing base-sensitive functional groups.…”

Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process

“…Recently, Wang and co-workers reported a novel metal-free borylation method using arylamines as the starting materials [33,34,35,36] (Scheme 1, Path 6). In this process, symmetrical B(pin)-B(pin) was utilized as the borylating reagent [37,38,39]. In order to obtain aryl B(dan) from arylamines, an additional step is required to complete the conversion (Scheme 1, Path 4).…”