Catalytic Enantioselective Synthesis of a cis-β-Boronyl Cyclobutylcarboxyester Scaffold and Its Highly Diastereoselective Nickel/Photoredox Dual-Catalyzed Csp3‒Csp2 Cross-Coupling to Access Elusive trans-β-Aryl/Heteroaryl Cyclobutylcarboxyesters
Nguyen, Kevin; Clement, Helen A.; Bernier, Louise; Coe, Jotham W.; Farrell, William; Helal, Christopher J.; Reese, Matthew R.; Sach, Neal W.; Lee, Jack C.; Hall, Dennis G.; ACS Catalysis  (2020) 404–413; doi:10.1021/acscatal.0c04520

data_4518342
_publ_section_title
;
 Catalytic Enantioselective Synthesis of a cis-\b-Boronyl
 Cyclobutylcarboxyester Scaffold and Its Highly Diastereoselective
 Nickel/Photoredox Dual-Catalyzed Csp3--Csp2 Cross-Coupling to Access
 Elusive trans-\b-Aryl/Heteroaryl Cyclobutylcarboxyesters
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              404
_journal_page_last               413
_journal_paper_doi               10.1021/acscatal.0c04520
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H15 B Br2 F3 K O2'
_chemical_formula_sum            'C18 H15 B Br2 F3 K O2'
_chemical_formula_weight         530.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0712(12)
_cell_length_b                   30.159(2)
_cell_length_c                   6.8657(5)
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.36
_cell_measurement_theta_min      2.64
_cell_volume                     4156.0(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.1192
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20900
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         2.644
_exptl_absorpt_coefficient_mu    7.078
_exptl_absorpt_correction_T_max  0.6193
_exptl_absorpt_correction_T_min  0.1627
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       needle
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0955P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2111
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4342
_reflns_number_total             7566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04520_si_002.cif
_cod_data_source_block           dgh1910
_cod_database_code               4518342
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.155
_shelx_estimated_absorpt_t_max   0.821
_shelx_res_checksum              84958
_shelx_hkl_checksum              38405