Electron‐Catalyzed Cross‐Coupling of Arylboron Compounds with Aryl Iodides

Abstract

Arylboroxines in combination with zinc chloride and potassium tert-butoxide were found to undergo the electron-catalyzed cross-coupling with aryl iodides to give the corresponding biaryls without the aid of transition-metal catalysis.

Manipulation of an electron by photoirradiation in the electron-catalyzed cross-coupling reaction

“…In 2012, we reported the first electron-catalyzed crosscoupling reaction, which uses aryl Grignard reagents and aryl halides to obtain biaryls with no aid of a transition metal catalysis (6). The electron catalysis (7) has been further applied to the crosscoupling reaction of various organometallic reagents with aryl/ alkenyl halides (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21). As shown in Fig.…”

Metal‐free catalytic activation and borylation of the ––H bond of 1‐methyl pyrrole using adamantane‐derived aminoborane frustrated Lewis pairs: A density functional theory study

“…[12,32,33] The -C sp 2 -H activation followed by -C sp 2 -H borylation of aromatic species generates organoboronates, and these are ubiquitous reagents especially for the Suzuki-Miyaura cross-coupling reactions as a building block for the formation of new bonds. [1,6,10,11,[47][48][49][50][51][52][53][54][55][56][57][58] Such coupling reactions are useful in the synthesis of pharmaceutical drugs, conducting polymers, molecular wires, liquid crystals, natural products, and in the supramolecular chemistry. [2,[59][60][61] Recently, the metal-free catalytic -C-H bond activation and dehydrogenative borylation of pyrrole, furan, and electron-rich thiophene using sterically hindered aminoborane (1-TMP-2-BH 2 -C 6 H 4 ) 2 as an FLP catalyst that bears bulky 2,2,6,6-tetramethyl piperidine as an LB have been reported.…”

Recent Synthesis Developments of Organoboron Compounds via Metal-Free Catalytic Borylation of Alkynes and Alkenes

“…Organoboron compounds play an important role in organic chemistry as they can be converted into a wide variety of functional groups [1,2,3,4,5,6,7,8,9,10,11,12,13]. Thus, the synthesis of different types of organoboron compounds continues to be an important research field [14,15,16,17,18,19,20].…”