References
13
22. Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL (1998) Rational development of practical
catalysts for aromatic carbon-nitrogen bond formation. Acc Chem Res 31:805–818
23. Wu W, Jiang H (2012) Palladium-catalyzed oxidation of unsaturated hydrocarbons using
molecular oxygen. Acc Chem Res 45:1736–1748
24. Xiao Q, Zhang Y, Wang J (2013) Diazo compounds and N-tosylhydrazones: novel crosscoupling partners in transition-metal-catalyzed reactions. Acc Chem Res 46:236–247
25. Yu D-G, Li B-J, Shi Z-J (2010) Exploration of new C–O electrophiles in cross-coupling
reactions. Acc Chem Res 43:1486–1495
26. Liu C, Ji CL, Zhou T, Hong X, Szostak M (2019) Decarbonylative phosphorylation of
carboxylic acids via redox-neutral palladium catalysis. Org Lett 21:9256–9261
27. Mo Y, Lu Z, Rughoobur G, Patil P, Gershenfeld N, Akinwande AI, Buchwald SL, Jensen
KF (2020) Microfluidic electrochemistry for single-electron transfer redox-neutral reactions.
Science 368:1352–1357
28. Nielsen MK, Shields BJ, Liu J, Williams MJ, Zacuto MJ, Doyle AG (2017) Mild, redoxneutral formylation of aryl chlorides through the photocatalytic generation of chlorine radicals.
Angew Chem Int Ed 56:7191–7194
29. Qi L-W, Li S, Xiang S-H, Wang J, Tan B (2019) Asymmetric construction of atropisomeric
biaryls via a redox neutral cross-coupling strategy. Nat Catal 2:314–323
30. Xie J, Jin H, Hashmi ASK (2017) The recent achievements of redox-neutral radical C–C
cross-coupling enabled by visible-light. Chem Soc Rev 46:5193–5203
31. Xuan J, Zeng TT, Feng ZJ, Deng QH, Chen JR, Lu LQ, Xiao WJ, Alper H (2015) Redox-neutral
alpha-allylation of amines by combining palladium catalysis and visible-light photoredox
catalysis. Angew Chem Int Ed 54:1625–1628
32. Zhou C, Lei T, Wei X-Z, Ye C, Liu Z, Chen B, Tung CH, Wu L-Z (2020) Metal-Free, redoxneutral, site-selective access to heteroarylamine via direct radical-radical cross-coupling
powered by visible light photocatalysis. J Am Chem Soc 142:16805–16813
33. Zhu C, Yue H, Nikolaienko P, Rueping M (2020) Merging electrolysis and nickel catalysis
in redox neutral cross-coupling reactions: experiment and computation for electrochemically
induced C–P and C–Se bonds formation. CCS Chemistry 2:179–190
34. Guan H, Zhang Q, Walsh PJ, Mao J (2020) Nickel/Photoredox-catalyzed asymmetric reductive
cross-coupling of racemic alpha-chloro esters with aryl iodides. Angew Chem Int Ed 59:5172–
5177
35. Kadunce NT, Reisman SE (2015) Nickel-catalyzed asymmetric reductive cross-coupling
between heteroaryl iodides and α-Chloronitriles. J Am Chem Soc 137:10480–10483
36. Li Y, Luo Y, Peng L, Li Y, Zhao B, Wang W, Pang H, Deng Y, Bai R, Lan Y, Yin G (2020)
Reaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura crosscoupling. Nat Commun 11:417
37. Mitsui A, Nagao K, Ohmiya H (2020) Copper-Catalyzed enantioselective reductive crosscoupling of aldehydes and imines. Org Lett 22:800–803
38. Poremba KE, Dibrell SE, Reisman SE (2020) Nickel-Catalyzed enantioselective reductive
cross-coupling reactions. ACS Catal 10:8237–8246
39. Tollefson EJ, Erickson LW, Jarvo ER (2015) Stereospecific intramolecular reductive crosselectrophile coupling reactions for cyclopropane synthesis. J Am Chem Soc 137:9760–9763
40. Zhong YW, Dong YZ, Fang K, Izumi K, Xu MH, Lin G-Q (2005) A highly efficient and
direct approach for synthesis of enantiopure beta-amino alcohols by reductive cross-coupling
of chiral N-tert-butanesulfinyl imines with aldehydes. J Am Chem Soc 127:11956–11957
41. Ashenhurst JA (2010) Intermolecular oxidative cross-coupling of arenes. Chem Soc Rev
39:540–548
42. Chen M, Zheng X, Li W, He J, Lei A (2010) Palladium-catalyzed aerobic oxidative crosscoupling reactions of terminal alkynes with alkylzinc reagents. J Am Chem Soc 132:4101–
4103
43. Hull KL, Sanford MS (2009) Mechanism of benzoquinone-promoted palladium-catalyzed
oxidative cross-coupling reactions. J Am Chem Soc 131:9651–9653
13
22. Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL (1998) Rational development of practical
catalysts for aromatic carbon-nitrogen bond formation. Acc Chem Res 31:805–818
23. Wu W, Jiang H (2012) Palladium-catalyzed oxidation of unsaturated hydrocarbons using
molecular oxygen. Acc Chem Res 45:1736–1748
24. Xiao Q, Zhang Y, Wang J (2013) Diazo compounds and N-tosylhydrazones: novel crosscoupling partners in transition-metal-catalyzed reactions. Acc Chem Res 46:236–247
25. Yu D-G, Li B-J, Shi Z-J (2010) Exploration of new C–O electrophiles in cross-coupling
reactions. Acc Chem Res 43:1486–1495
26. Liu C, Ji CL, Zhou T, Hong X, Szostak M (2019) Decarbonylative phosphorylation of
carboxylic acids via redox-neutral palladium catalysis. Org Lett 21:9256–9261
27. Mo Y, Lu Z, Rughoobur G, Patil P, Gershenfeld N, Akinwande AI, Buchwald SL, Jensen
KF (2020) Microfluidic electrochemistry for single-electron transfer redox-neutral reactions.
Science 368:1352–1357
28. Nielsen MK, Shields BJ, Liu J, Williams MJ, Zacuto MJ, Doyle AG (2017) Mild, redoxneutral formylation of aryl chlorides through the photocatalytic generation of chlorine radicals.
Angew Chem Int Ed 56:7191–7194
29. Qi L-W, Li S, Xiang S-H, Wang J, Tan B (2019) Asymmetric construction of atropisomeric
biaryls via a redox neutral cross-coupling strategy. Nat Catal 2:314–323
30. Xie J, Jin H, Hashmi ASK (2017) The recent achievements of redox-neutral radical C–C
cross-coupling enabled by visible-light. Chem Soc Rev 46:5193–5203
31. Xuan J, Zeng TT, Feng ZJ, Deng QH, Chen JR, Lu LQ, Xiao WJ, Alper H (2015) Redox-neutral
alpha-allylation of amines by combining palladium catalysis and visible-light photoredox
catalysis. Angew Chem Int Ed 54:1625–1628
32. Zhou C, Lei T, Wei X-Z, Ye C, Liu Z, Chen B, Tung CH, Wu L-Z (2020) Metal-Free, redoxneutral, site-selective access to heteroarylamine via direct radical-radical cross-coupling
powered by visible light photocatalysis. J Am Chem Soc 142:16805–16813
33. Zhu C, Yue H, Nikolaienko P, Rueping M (2020) Merging electrolysis and nickel catalysis
in redox neutral cross-coupling reactions: experiment and computation for electrochemically
induced C–P and C–Se bonds formation. CCS Chemistry 2:179–190
34. Guan H, Zhang Q, Walsh PJ, Mao J (2020) Nickel/Photoredox-catalyzed asymmetric reductive
cross-coupling of racemic alpha-chloro esters with aryl iodides. Angew Chem Int Ed 59:5172–
5177
35. Kadunce NT, Reisman SE (2015) Nickel-catalyzed asymmetric reductive cross-coupling
between heteroaryl iodides and α-Chloronitriles. J Am Chem Soc 137:10480–10483
36. Li Y, Luo Y, Peng L, Li Y, Zhao B, Wang W, Pang H, Deng Y, Bai R, Lan Y, Yin G (2020)
Reaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura crosscoupling. Nat Commun 11:417
37. Mitsui A, Nagao K, Ohmiya H (2020) Copper-Catalyzed enantioselective reductive crosscoupling of aldehydes and imines. Org Lett 22:800–803
38. Poremba KE, Dibrell SE, Reisman SE (2020) Nickel-Catalyzed enantioselective reductive
cross-coupling reactions. ACS Catal 10:8237–8246
39. Tollefson EJ, Erickson LW, Jarvo ER (2015) Stereospecific intramolecular reductive crosselectrophile coupling reactions for cyclopropane synthesis. J Am Chem Soc 137:9760–9763
40. Zhong YW, Dong YZ, Fang K, Izumi K, Xu MH, Lin G-Q (2005) A highly efficient and
direct approach for synthesis of enantiopure beta-amino alcohols by reductive cross-coupling
of chiral N-tert-butanesulfinyl imines with aldehydes. J Am Chem Soc 127:11956–11957
41. Ashenhurst JA (2010) Intermolecular oxidative cross-coupling of arenes. Chem Soc Rev
39:540–548
42. Chen M, Zheng X, Li W, He J, Lei A (2010) Palladium-catalyzed aerobic oxidative crosscoupling reactions of terminal alkynes with alkylzinc reagents. J Am Chem Soc 132:4101–
4103
43. Hull KL, Sanford MS (2009) Mechanism of benzoquinone-promoted palladium-catalyzed
oxidative cross-coupling reactions. J Am Chem Soc 131:9651–9653