Cartesian coordinates and electronic energies (EE, in hatree) of relevant compounds. 10 PropylRad, EE= -118.273347 C -1.32976 -0.05909 0.49291 H -1.69689 -1.03266 0.83501 H -2.00369 0.52968 -0.13860 C 0.11217 0.28259 0.58723 H 0.52851 -0.09502 1.53941 H 0.23937 1.38056 0.61495 C 0.93856 -0.28091 -0.57038 H 2.00369 -0.01333 -0.47608 H 0.58018 0.10368 -1.53941 H 0.87074 -1.38056 -0.60943 21 Alkyl/Aryl Coupled Product, EE= -349.647201 C -0.59006 -3.41152 -0.49160 H -0.29728 -3.67047 -1.52336 H -1.60895 -3.79636 -0.33034 H 0.08405 -3.96434 0.18461 C -0.50137 -1.91755 -0.25436 H -1.20313 -1.37852 -0.91838 H -0.82467 -1.66976 0.77424 C 0.90451 -1.36542 -0.47372 H 1.60895 -1.89293 0.19658 H 1.22818 -1.59959 -1.50533 C 0.98680 0.11443 -0.23706 C 1.25316 0.62200 1.03890 H 1.45145 -0.07713 1.86003 C 1.27395 1.99456 1.27398 H 1.48899 2.37202 2.27825 C 1.02526 2.88580 0.23200 H 1.04389 3.96434 0.41368 C 0.75597 2.39403 -1.04378 H 0.56231 3.08674 -1.86834 C 0.73648 1.02048 -1.27300 H 0.52656 0.63607 -2.27825 51 B1, EE= -2524.241194 Ni -0.13412 0.60078 0.02541 C 1.42016 -0.65421 -3.59443 C 0.76525 -0.03562 -2.50859 C -0.54017 0.46044 -2.73975 C -1.13027 0.40009 -3.99413 C -0.45591 -0.19441 -5.06186 C 0.81149 -0.72804 -4.84287 N 1.19659 0.10144 -1.22073 N -1.19567 1.09326 -1.58548 C -2.61868 0.73599 -1.50628 C 2.44679 -0.06865 -0.69967 C 2.48832 -0.09050 0.71505 C 3.68030 -0.25585 1.40581 C 4.88660 -0.36685 0.71243 C 4.87066 -0.30278 -0.67849 C 3.67901 -0.15800 -1.38102 N 1.18726 0.01064 1.39292 C 1.25902 0.87456 2.57925 C -1.47708 1.10491 1.28319 C 0.74336 -1.34038 1.78596 C -1.05451 2.55776 -1.69543 H -2.13104 0.81186 -4.15461 H -0.92626 -0.25063 -6.04665 H 1.34138 -1.22493 -5.66157 H 2.39451 -1.12177 -3.44736 H 3.70783 -0.06682 -2.46750 H 5.81076 -0.35733 -1.23635 H 5.82575 -0.48642 1.25821 H 3.68492 -0.29384 2.49914 H -3.16925 1.07996 -2.39925 H -3.06722 1.20365 -0.62044 H -2.71958 -0.35628 -1.42150 H 0.01276 2.81920 -1.74696 H -1.50819 3.04148 -0.81763 H -1.55450 2.92471 -2.61136 H 1.96468 0.47211 3.32685 H 0.26671 0.94741 3.04253 H 1.58750 1.88152 2.28172 H 0.68468 -1.98002 0.89293 H 1.46138 -1.78933 2.49762 H -0.24741 -1.28226 2.26066 C -1.58474 2.42034 1.76643 C -2.56597 2.79713 2.68610 C -3.47965 1.85683 3.15909 C -2.41402 0.18170 1.77848 C -3.39883 0.54312 2.70049 H -0.86781 3.18562 1.43310 H -2.61493 3.83292 3.03944 H -4.24987 2.14603 3.88060 H -2.39592 -0.85958 1.42326 H -4.11170 -0.20662 3.06079 61 B2, EE= -2642.542537 Ni -0.81976 -0.05537 0.40116 C 1.33947 0.66671 -3.16459 C 0.40233 0.39531 -2.14167 C -0.95280 0.25253 -2.54560 C -1.33761 0.44700 -3.86747 C -0.40123 0.77274 -4.84721 C 0.94012 0.85553 -4.48189 N 0.67031 0.17004 -0.82054 C -2.23898 -0.60898 1.59969 C -2.43077 -0.20292 3.04510 C -3.32533 -1.17167 3.80224 N -1.89892 -0.21319 -1.54275 C -2.04112 -1.67020 -1.63767 C 1.87215 0.34215 -0.17359 C 2.02626 -0.39179 1.03609 C 3.17575 -0.27329 1.80714 C 4.19696 0.60216 1.43118 C 4.04145 1.36322 0.27831 C 2.90078 1.23957 -0.51185 N 0.91221 -1.22755 1.42327 C 0.79594 -1.46976 2.85002 C -1.08116 1.66069 1.17463 C 0.93253 -2.50289 0.70464 C -3.20591 0.42211 -1.64485 H -2.38929 0.33194 -4.14841 H -0.71585 0.93974 -5.88043 H 1.70006 1.07237 -5.23930 H 2.40258 0.70623 -2.92329 H 2.77601 1.89502 -1.37551 H 4.81300 2.08390 -0.00969 H 5.09340 0.69761 2.04939 H 3.28031 -0.85606 2.72663 H -2.46041 -1.96920 -2.61904 H -2.71189 -2.04170 -0.84491 H -1.05612 -2.15133 -1.52916 H -3.08373 1.51356 -1.69224 H -3.81801 0.16508 -0.76570 H -3.76536 0.09090 -2.54148 H 1.59909 -2.13038 3.23536 H -0.16588 -1.96597 3.05978 H 0.82746 -0.51920 3.40381 H 1.02947 -2.32603 -0.37634 H 1.78342 -3.13160 1.03667 H -1.97082 -1.69311 1.53931 H -3.19082 -0.47551 1.04915 H -1.45740 -0.12061 3.56099 H -2.85759 0.81448 3.08895 H -3.49760 -0.85020 4.84215 H -4.31166 -1.26888 3.31643 H -2.88313 -2.18358 3.83688 H -0.00219 -3.05941 0.89530 C -0.01558 2.17623 1.91688 C -0.06288 3.48298 2.40671 C -1.17470 4.28681 2.16747 C -2.19986 2.46502 0.94984 C -2.24302 3.77268 1.43665 H 0.88317 1.57693 2.10901 H 0.78581 3.87344 2.97746 H -1.21057 5.30966 2.55375 H -3.06892 2.07603 0.41089 H -3.12764 4.38978 1.24823 61 TS_B2,B3 , EE= -2642.539524 Ni 0.33160 -0.50884 -0.39318 C -3.65765 0.62425 0.39362 C -2.42503 -0.00469 0.10100 C -2.45734 -1.41794 -0.05841 C -3.62983 -2.14045 0.13258 C -4.82035 -1.50130 0.47441 C -4.82082 -0.11185 0.57967 N -1.22674 0.60767 -0.12236 C 1.93219 -1.50797 -0.97246 C 3.41971 -1.22032 -0.93688 C 4.13961 -1.80798 -2.13903 N -1.23964 -2.06231 -0.52997 C -1.31050 -2.24715 -1.98243 C -0.90922 1.92484 0.12007 C 0.17886 2.45668 -0.63244 C 0.62164 3.75817 -0.41971 C 0.02563 4.56827 0.54919 C -1.01575 4.05298 1.31218 C -1.47399 2.75440 1.10531 N 0.79542 1.57309 -1.58866 C 2.14784 1.91951 -1.97549 C 1.54581 -0.81560 1.02056 C -0.02601 1.41582 -2.78821 C -0.96945 -3.33530 0.12287 H -3.62295 -3.22774 0.00331 H -5.73324 -2.07971 0.63744 H -5.75072 0.41730 0.81160 H -3.70120 1.71332 0.45417 H -2.25215 2.35070 1.75647 H -1.47376 4.66209 2.09765 H 0.38681 5.58773 0.70889 H 1.44947 4.15719 -1.01256 H -2.14087 -2.92596 -2.26247 H -0.36720 -2.67739 -2.35994 H -1.48221 -1.27711 -2.47476 H -0.99505 -3.20575 1.21469 H 0.02732 -3.70136 -0.17345 H -1.70038 -4.11914 -0.15711 H 2.19438 2.83945 -2.59555 H 2.57774 1.10098 -2.57749 H 2.78425 2.07051 -1.08986 H -1.05764 1.15628 -2.51250 H -0.04260 2.35115 -3.38495 H 1.54484 -1.25037 -1.99248 H 1.74869 -2.58727 -0.81691 H 3.59451 -0.13100 -0.89255 H 3.85651 -1.61886 -0.00405 H 5.22617 -1.63307 -2.09159 H 3.98206 -2.89809 -2.20693 H 3.77331 -1.36963 -3.08427 H 0.38442 0.61102 -3.42400 C 2.10070 0.39010 1.47279 C 2.68502 0.47319 2.73487 C 2.75313 -0.65054 3.55645 C 1.62960 -1.94153 1.84595 C 2.22348 -1.85694 3.10496 H 2.06030 1.29197 0.85028 H 3.08991 1.43070 3.07690 H 3.22244 -0.58703 4.54229 H 1.24381 -2.90737 1.50816 H 2.27534 -2.74975 3.73615 40 B3, EE = -2292.918795 Ni 0.70803 -1.34293 -0.09066 C 2.90412 2.13697 -0.39141 C 2.08561 0.99149 -0.51844 C 2.09225 0.34198 -1.79211 C 2.82932 0.84141 -2.85635 C 3.61595 1.98468 -2.70664 C 3.64824 2.61464 -1.46412 N 1.33607 0.38162 0.43316 N 1.24731 -0.84798 -1.94515 C 1.92191 -1.95696 -2.61971 C 0.93923 0.74147 1.67908 C 0.31783 -0.29730 2.44003 C -0.15523 -0.07069 3.72460 C -0.06512 1.19492 4.30635 C 0.50828 2.22904 3.56913 C 1.00125 2.01623 2.28682 N 0.24435 -1.62864 1.82723 C -1.06568 -2.26335 1.97197 C 1.30094 -2.49477 2.36720 C 0.00200 -0.49946 -2.64225 H 2.79798 0.33142 -3.82546 H 4.20004 2.36814 -3.54705 H 4.27567 3.50028 -1.32043 H 2.98441 2.63387 0.57712 H 1.40837 2.85886 1.72500 H 0.56877 3.23399 3.99935 H -0.44665 1.36811 5.31577 H -0.60894 -0.89268 4.28916 H 2.13140 -1.74157 -3.68675 H 1.28046 -2.85189 -2.57393 H 2.87155 -2.17671 -2.11052 H -0.50492 0.31123 -2.09860 H -0.66687 -1.37462 -2.67684 H 0.20531 -0.16099 -3.67859 H -1.29464 -2.53121 3.02300 H -1.08721 -3.18856 1.37366 H -1.84809 -1.58501 1.60173 H 2.27851 -2.01379 2.21632 H 1.15554 -2.67416 3.45190 H 1.29821 -3.46327 1.84136 52 E1, EE= -5098.010154 Ni -0.99625 -0.04884 -0.25588 C 0.61817 0.06804 -1.29274 C 0.00491 2.13698 1.38792 C 0.60149 0.91141 1.78862 C 1.85003 0.97689 2.42875 C 2.43873 2.20212 2.73296 C 1.81244 3.39411 2.39003 C 0.60005 3.35235 1.69962 N -0.08009 -0.23140 1.40199 Br -2.59209 0.22877 -1.97607 N -1.19282 2.03818 0.59978 C -1.40671 3.13459 -0.33417 C 0.18002 -1.51499 1.82101 C 0.87309 -1.88996 2.99291 C 1.07718 -3.22626 3.31360 C 0.60564 -4.24354 2.48693 C -0.13380 -3.89983 1.35823 C -0.36421 -2.56670 1.03568 N -1.24761 -2.19112 -0.04439 C -2.64144 -2.28771 0.41739 C -1.06211 -2.94248 -1.28466 C -2.38989 1.84382 1.42694 H 0.12247 4.28594 1.39050 H 2.27229 4.35605 2.63118 H 3.41310 2.21687 3.23003 H 2.39500 0.05837 2.64965 H 1.22042 -1.12053 3.68305 H 1.61716 -3.47399 4.23238 H 0.78681 -5.29338 2.73063 H -0.55719 -4.68525 0.72437 H -1.70906 4.06808 0.18027 H -2.20259 2.84821 -1.03930 H -0.48473 3.32742 -0.90185 H -2.22773 1.02637 2.14474 H -3.24562 1.58980 0.77938 H -2.62889 2.76568 1.99355 H -2.89063 -3.32975 0.69694 H -3.32074 -1.94383 -0.37687 H -2.78404 -1.65023 1.30631 H -0.00227 -2.92435 -1.57655 H -1.39296 -3.99397 -1.18569 H -1.65190 -2.46168 -2.08010 C 1.67745 -0.80268 -1.05907 C 2.85888 -0.66102 -1.79196 C 2.98045 0.34615 -2.74514 C 0.72375 1.07485 -2.24950 C 1.91241 1.20980 -2.97140 H 1.61758 -1.59562 -0.30379 H 3.69266 -1.34388 -1.60019 H 3.90775 0.45581 -3.31481 H -0.11759 1.73725 -2.46777 H 1.98941 1.99502 -3.73018 62 TS_E1,E2 , EE= -5216.274880 Ni 0.40370 -0.18048 -0.18764 C 0.90320 1.82915 1.72252 H -0.01460 2.30070 1.34726 H 1.79784 1.95143 1.10184 C 1.12834 1.81074 3.19330 H 1.88059 1.04382 3.45866 H 0.20207 1.54429 3.73152 C 1.62191 3.17116 3.68437 H 1.78868 3.16764 4.77327 H 2.57246 3.44784 3.19968 H 0.89178 3.96537 3.45868 C 2.33869 -0.41977 -0.20472 C -0.97061 2.33184 -0.94414 C -1.89063 1.50261 -0.25345 C -3.09437 2.09446 0.18858 C -3.35112 3.44068 -0.03416 C -2.43173 4.24498 -0.70708 C -1.24041 3.67975 -1.15836 N -1.46621 0.24032 0.05390 Br 0.20757 -1.89565 -1.86112 N 0.21984 1.68168 -1.45882 C 1.39152 2.55699 -1.51700 C -2.26805 -0.84172 0.32878 C -3.60777 -1.00038 -0.06253 C -4.30218 -2.17093 0.23013 C -3.67873 -3.21229 0.90876 C -2.33926 -3.08012 1.28598 C -1.63529 -1.92345 0.98960 N -0.24924 -1.72624 1.38059 C 0.55426 -2.94801 1.35709 C -0.24274 -1.15455 2.72798 C -0.06681 1.20222 -2.82419 H -0.51943 4.30260 -1.69531 H -2.63824 5.30380 -0.88233 H -4.28359 3.87402 0.34035 H -3.80444 1.49345 0.76177 H -4.09359 -0.20905 -0.63897 H -5.34119 -2.27407 -0.09664 H -4.21938 -4.13640 1.12918 H -1.84218 -3.90523 1.80381 H 1.29822 3.30707 -2.32422 H 2.28818 1.95200 -1.71835 H 1.52600 3.08899 -0.56588 H -0.93365 0.52935 -2.81976 H 0.79373 0.64163 -3.21777 H -0.27388 2.06880 -3.48123 H 0.25909 -3.64887 2.16153 H 1.61327 -2.68782 1.50377 H 0.45389 -3.43780 0.37946 H -0.81012 -0.21239 2.73828 H -0.70491 -1.85413 3.45240 H 0.79009 -0.95482 3.05465 C 2.99043 -0.52668 1.02747 C 4.38483 -0.57118 1.10927 C 5.15433 -0.52146 -0.04933 C 3.12396 -0.40139 -1.36253 C 4.51723 -0.43781 -1.28553 H 2.41792 -0.55791 1.96151 H 4.86677 -0.64427 2.08982 H 6.24606 -0.55937 0.00960 H 2.65136 -0.38050 -2.35048 H 5.10788 -0.41830 -2.20721 62 E2, EE= -5216.304288 Ni 0.59237 -0.09994 0.08232 C 0.82189 1.28943 1.46150 H -0.19382 1.32930 1.90058 H 0.95898 2.21753 0.87440 C 1.85758 1.19815 2.56308 H 2.85937 1.43465 2.16382 H 1.94938 0.15546 2.93095 C 1.53219 2.11553 3.73101 H 2.30872 2.08505 4.51273 H 1.43585 3.16309 3.39741 H 0.57207 1.83995 4.20341 C 2.50113 0.04049 -0.03418 C -1.56357 2.42740 -0.66919 C -2.14868 1.29015 -0.02383 C -3.32577 1.46819 0.74418 C -3.85763 2.72632 0.95825 C -3.23237 3.84288 0.39511 C -2.10501 3.69262 -0.40603 N -1.47284 0.10694 -0.02305 Br 0.65918 -1.70146 -1.75738 N -0.48735 2.23267 -1.53334 C 0.27875 3.40345 -1.89249 C -2.11485 -1.09650 0.04321 C -3.32011 -1.37190 -0.63454 C -3.80844 -2.66807 -0.69263 C -3.11481 -3.70474 -0.06634 C -1.93330 -3.44632 0.63148 C -1.43028 -2.15444 0.69934 N -0.27967 -1.77799 1.46067 C 0.68815 -2.84561 1.66949 C -0.70002 -1.22403 2.75280 C -0.70785 1.37215 -2.69394 H -1.66094 4.57851 -0.86392 H -3.63739 4.84379 0.56890 H -4.74103 2.84666 1.59070 H -3.75928 0.59334 1.23838 H -3.82089 -0.56051 -1.17164 H -4.72327 -2.87992 -1.25242 H -3.49426 -4.72864 -0.12206 H -1.40643 -4.26952 1.11903 H -0.28262 4.09804 -2.55304 H 1.17622 3.08719 -2.44567 H 0.60359 3.95273 -0.99468 H -1.33087 0.50427 -2.44386 H 0.25290 0.96799 -3.05036 H -1.19058 1.94694 -3.51089 H 0.28043 -3.66640 2.29248 H 1.55355 -2.42833 2.20637 H 1.02057 -3.23554 0.69506 H -1.42605 -0.41030 2.61231 H -1.17118 -2.00917 3.37732 H 0.17315 -0.82113 3.28746 C 3.40672 -0.89220 0.47234 C 4.77898 -0.73328 0.27749 C 5.27072 0.35552 -0.43921 C 3.00182 1.12336 -0.76176 C 4.37291 1.28036 -0.96686 H 3.05595 -1.77015 1.02208 H 5.47062 -1.47732 0.68639 H 6.34719 0.47894 -0.59041 H 2.31399 1.87073 -1.17329 H 4.74064 2.13818 -1.53981 62 TS_E2,E3 , EE = -5216.297697 Ni 0.58389 -0.21323 -0.00034 C 0.95446 1.54691 0.96467 H -0.06361 1.45270 1.39203 H 0.87006 2.21064 0.08562 C 1.80374 2.21232 2.02929 H 2.82028 2.42040 1.65079 H 1.94276 1.53033 2.88909 C 1.15043 3.50210 2.49951 H 1.74590 4.00611 3.27757 H 1.02930 4.21164 1.66207 H 0.14235 3.31959 2.91173 C 2.41963 0.25531 0.28169 C -1.73495 2.22275 -0.81355 C -2.20343 1.14596 0.00968 C -3.20845 1.40828 0.97282 C -3.65757 2.69587 1.20462 C -3.12835 3.75596 0.46048 C -2.18519 3.52113 -0.53391 N -1.52364 -0.03515 -0.01032 Br 0.81244 -1.74443 -1.87923 N -0.84171 1.94086 -1.83632 C -0.10026 3.03508 -2.41258 C -2.12322 -1.23064 0.24909 C -3.43612 -1.54702 -0.16355 C -3.92869 -2.83398 -0.01714 C -3.13035 -3.82587 0.55477 C -1.83746 -3.52680 0.98895 C -1.32636 -2.24266 0.85079 N -0.04175 -1.84510 1.35449 C 0.94222 -2.92759 1.37107 C -0.17998 -1.25281 2.68895 C -1.20809 0.94479 -2.83765 H -1.81945 4.36074 -1.12911 H -3.46951 4.77846 0.64564 H -4.39836 2.88467 1.98606 H -3.55663 0.57996 1.59800 H -4.03151 -0.77285 -0.65750 H -4.93465 -3.07529 -0.37111 H -3.51381 -4.84390 0.66395 H -1.22942 -4.31269 1.44270 H -0.71881 3.67553 -3.07709 H 0.72026 2.62505 -3.02274 H 0.34213 3.67110 -1.62895 H -1.83383 0.15305 -2.40757 H -0.30713 0.44424 -3.22533 H -1.75777 1.42815 -3.67083 H 0.71070 -3.68327 2.14669 H 1.93471 -2.50729 1.58478 H 0.98537 -3.38981 0.37467 H -0.90760 -0.42687 2.67418 H -0.52175 -2.00693 3.42604 H 0.79171 -0.85301 3.01932 C 3.22926 -0.29928 1.28032 C 4.61849 -0.31049 1.15831 C 5.23268 0.25636 0.04506 C 3.05397 0.83694 -0.82822 C 4.43884 0.83336 -0.94785 H 2.78108 -0.70378 2.19539 H 5.22529 -0.75945 1.95133 H 6.32247 0.25591 -0.04715 H 2.44508 1.28298 -1.62490 H 4.90496 1.28124 -1.83120 41 E3, EE= -4866.758159 Ni -0.01909 -0.75602 -0.02532 C -2.29884 0.86411 0.05792 C -1.19182 1.72472 -0.07915 C -1.46615 3.08758 -0.32177 C -2.77621 3.55358 -0.34255 C -3.85399 2.69703 -0.13176 C -3.60317 1.33873 0.05580 N 0.02578 1.09666 -0.00541 Br -0.07604 -3.10822 -0.04996 N -1.98226 -0.56145 0.19163 C -2.72863 -1.33509 -0.82021 C 1.27236 1.66335 0.08004 C 1.61228 3.00596 0.35090 C 2.94332 3.40757 0.38003 C 3.97842 2.50451 0.15023 C 3.66221 1.16415 -0.06540 C 2.33645 0.75328 -0.07611 N 1.95129 -0.65221 -0.23914 C 2.65864 -1.48172 0.75634 C 2.25791 -1.10486 -1.61036 C -2.31087 -1.02687 1.55344 H -4.44118 0.64781 0.18977 H -4.87984 3.07322 -0.13628 H -2.95472 4.61569 -0.53640 H -0.65644 3.78307 -0.53860 H 0.83713 3.73503 0.58320 H 3.17301 4.45551 0.59588 H 5.02126 2.83049 0.16152 H 4.46585 0.43649 -0.21462 H -3.81653 -1.21714 -0.67807 H -2.46292 -2.39654 -0.74260 H -2.45901 -0.96944 -1.82200 H -1.74602 -0.42619 2.28214 H -2.02969 -2.08460 1.65726 H -3.39070 -0.90692 1.75506 H 3.75110 -1.41313 0.61677 H 2.34237 -2.52735 0.65659 H 2.40579 -1.12457 1.76555 H 1.72349 -0.46249 -2.32634 H 3.34244 -1.03345 -1.80975 H 1.92571 -2.14529 -1.73592